Boron tribromide → HCID 66819815, compound

HRID 880825Notes

Reaction equation

HRID 880825 reaction equation
[ClH:1].[F:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C)[CH:15]=3)[NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[ClH:1].[F:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=3)[NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66819811HCID 66819811, compound

Product 1

HCID 66819815HCID 66819815, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 68 mg (0.166 mmol) of 7-fluoro-3-(3-methoxy-phenyl)-4-(3-piperidin-1-yl-propoxy)-2H-isoquinolin-1-one hydrochloride (cmpd. 43) in anhydrous dichloromethane (1 mL), boron tribromide (1M in dichloromethane) (1 mL, 1 mmol) was added and the mixture was stirred overnight at room temperature under argon atmosphere. The solvent was concentrated under reduced pressure and the crude was purified by flash chromatography (eluant: starting with dichloromethane/methanol/acetone/7N ammonia in methanol: 93/3/3/1 to 88/6/5/1) to afford the free base, which was then converted into the hydrochloride salt according to common chemical procedures (58 mg of the title compound, 81%).

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customthe crude was purified by flash chromatography (eluant: starting with dichloromethane/methanol/acetone/7N ammonia in methanol: 93/3/3/1 to 88/6/5/1)
  3. customto afford the free base, which

Sources & evidence

ORD record
ord-670df3ed721e484e8e4c7e0466e6efb5
Source dataset
uspto-grants-2015_03
Patent number
US08993594B2

Reaction notes

Loading…