LOS ANGELES (AP) — Chris Brown was arrested Friday and will be held without bail on a warrant issued by probation officials in the latest legal entanglement for the R&B singer who has struggled to put his 2009 attack on Rihanna behind him. 
 
 FILE - In this Feb. 3, 2014 file photo, R&B; singer Chris Brown arrives at a Los Angeles Superior Court for a probation review hearing in Los Angeles. The Los Angeles Sheriff’s Department said that Brown... (Associated Press) 
 
 The warrant was issued by the judge overseeing Brown's case after he was informed Friday morning that the singer had been discharged from rehab "for failure to comply with rules and regulations of the program." No further details were released, but more information will be presented to Superior Court Judge James R. Brandlin when Brown appears in his courtroom on Monday afternoon. 
 
 Sheriff's officials said Brown was cooperative when he was arrested at a Malibu treatment facility where he had been staying and transported to a jail facility in downtown Los Angeles. 
 
 Brown had been ordered to remain in rehab for anger management treatment. A January letter from the facility stated that the singer was also being treated for bipolar disorder, post-traumatic stress disorder and past substance abuse. 
 
 An email sent to Brown's attorney Mark Geragos was not immediately returned. A probation spokeswoman declined to comment on what prompted Brown's arrest. 
 
 Brown's probation for the Rihanna assault had been scheduled to end this year, but a judge revoked it last year after Brown was arrested on a misdemeanor assault charge in Washington, D.C. That case is pending. 
 
 Brandlin rejected a Los Angeles prosecutor's request to send Brown to jail because of the Washington case, citing his progress in rehab. He has ordered Brown to stop smoking marijuana and take only prescribed medications; the singer has not failed any drug screenings since the order was made. 
 
 In addition to getting treatment, the singer remained under strict orders to complete 1,000 hours of community labor this year. A probation report dated Feb. 26 stated that Brown had completed 250 hours and that he was being cooperative with probation officials. 
 
 Brown's attempts at treatment have not been without difficulties. 
 
 A rehab center where Brown was voluntarily staying reported to Brandlin that the singer threw a rock through his mother's window during a joint counseling session in November. The judge then ordered Brown to remain in treatment for another three months and renewed that order at a hearing on Feb. 28. 
 
 A probation officer interviewed Brown for the February report, saying the singer was grateful to be in rehab and "looks forward to staying out of trouble." 
 
 "He remains thankful to the court for the opportunity to find out and learn more about himself, his anger issues and the type of person he wants to become, which is a man who is able to better himself and be a positive role model," the report states. 
 
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 Anthony McCartney can be reached at http://twitter.com/mccartneyAP 

 Story highlights The singer was "cooperative when taken into custody," sheriff's statement says 
 
 Brown has been in court-ordered rehab for the past four months 
 
 He is serving five years probation for the beating of Rihanna 
 
 Details were not immediately available about why Brown, 24, was kicked out of the Malibu facility where he has been treated for the past four months. 
 
 Nor was it clear exactly why he was taken into immediate custody, but he had been serving a five-year probation sentence when he entered rehab. That sentence stemmed from a 2009 assault on then-girlfriend Rihanna. 
 
 He was "cooperative when taken into custody" as he was picked up from the facility and taken to the Los Angeles County men's central jail where he was being held without bail Friday afternoon, a sheriff's department statement said. 
 
 His lawyer and representatives did not immediately respond to CNN calls for comment. 
 
 Brown's legal troubles began five years ago when he beat Rihanna as the two were in a rented Lamborghini on a Hollywood street. He pleaded guilty to felony assault in June 2009, which resulted in a sentence of five years of probation and 1,400 hours of community labor. 
 
 The judge has revoked Brown's probation twice in the last year, most recently because of his arrest on a sidewalk near the White House after allegedly punching a man. 
 
 Brown voluntarily entered a rehab program a day after being released from a Washington jail in October, but he was kicked out a few days later for "throwing a rock through his mother's car window" after a family session at the center, a probation report said. Brown was upset because his mother said she wanted him to stay in treatment, the report said. 
 
 "Mr. Brown preceded to walk outside and pick up a rock and threw it through his mother's car window and it shattered," according to letter from the rehab center included in the probation report. 
 
 His probation was revoked last November, but the judge allowed him to stay out of jail by entering a 90-day anger management and drug rehab program. Although he completed that program last month, the judge ordered him to remain a resident at the Malibu treatment facility until another hearing on April 23. 
 
 Brown's probation officer reported at a hearing last month that the singer "continues to make great improvement" in dealing with anger, stress and drugs, but the judge decided he could not go free until after his trial for an assault charge in Washington on April 17. If he is convicted in that case, the judge would decide at an April 23 hearing if Brown should complete his probation in jail. 
 
 Brown has been working on a highway cleanup labor crew in Los Angeles three days a week to fulfill the 750 hours of service remaining in his probation requirements, his probation report said. At that rate, Brown could complete the labor in mid-October and possibly be free from probation requirements by the end of the year.
– It's hard to keep track of Chris Brown's legal run-ins since his assault of Rihanna in 2009, but this part's easy: He is now in jail, reports CNN. Brown was taken into custody yesterday after a Malibu rehab facility kicked him out, putting him in violation of his probation. It's not clear what Brown did to get the boot, but TMZ doesn't think it involves drugs, violence, or the "inappropriate relationship" he was found to be having with a female staffer earlier this month. Nor is it clear how long he will have to remain in jail, but his next court appearance isn't until Monday, reports AP. Brown had been in the rehab facility for about four months, after he got arrested on assault charges in DC and later hurled a rock through a window of his mother's car.