California Gov. Gavin Newsom on Tuesday requested a federal judge issue a temporary restraining order—and asked it be issued by 4 p.m. EDT— blocking President Donald Trump from deploying the National Guard and Marines to Los Angeles where anti-immigration protests have ensued in recent days.

6:30 p.m.: More than 100 people gathered at the immigration services building and detention center in downtown Los Angeles to protest the raids. DHS officers fired pepper balls at the protesters before the Los Angeles Police Department dispersed the crowd.

Tear gas and flash bangs were deployed to disperse crowds protesting immigration raids in downtown Los Angeles after dozens of people were arrested by federal immigration agents Friday, including a prominent union leader.