Boron tribromide → HCID 66599603, compound

HRID 1909055Notes

Reaction equation

HRID 1909055 reaction equation
[CH3:1][N:2]([CH3:38])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25]C)=[C:21]([C:27]5[C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[CH:30]=[N:29][CH:28]=5)[CH:20]=4)=[O:18])[NH:14][C:13]=3[CH:37]=2)[CH2:5][CH2:4]1.B(Br)(Br)Br>ClCCl.[Cl-].[NH4+]>[CH3:1][N:2]([CH3:38])[CH:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([C:17]([C:19]4[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([C:27]5[C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[CH:30]=[N:29][CH:28]=5)[CH:20]=4)=[O:18])[NH:14][C:13]=3[CH:37]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 66599789HCID 66599789, compound

Product 1

HCID 66599603HCID 66599603, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a cooled (−78° C.) solution of [6-(4-Dimethylamino-piperidin-1-yl)-1H-benzoimidazol-2-yl]-(3-isoquinolin-4-yl-4-methoxy-phenyl)-methanone (6 mg, 0.012 mmol) in dichloromethane (6 mL) was added boron tribromide (0.118 mL, 10 eq) dropwise resulting in bright yellow solution. The reaction mixture was allowed to warm, diluted with saturated ammonium chloride solution, and extracted with dichloromethane. The organics were dried over Na2SO4, filtered, concentrated and purified by HPLC (Deltapak C18, acetonitrile: 0.1% trifluoroacetic acid), then neutralized using PL-HCO3 SPE to obtain 1 mg [6-(4-dimethylamino-piperidin-1-yl)-1H-benzoimidazol-2-yl]-(4-hydroxy-3-isoquinolin-4-yl-phenyl)-methanone in 20% yield. MS m/z 492.4 (M+H)+.

Workup

  1. customdropwise resulting in bright yellow solution
  2. temperatureto warm
  3. extractionextracted with dichloromethane
  4. dry with materialThe organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by HPLC (Deltapak C18, acetonitrile: 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-c5092c7e28c744299d9df4038a2f50c3
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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