Water → HCID 58437488, compound

HRID 881644Notes

Reaction equation

HRID 881644 reaction equation
C([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:21]C)=[C:17]([F:20])[CH:18]=3)[C:13]([C:23]#[N:24])=[CH:12]2)=[CH:7][CH:6]=1)C.B(Br)(Br)Br.O>ClCCl>[C:23]([C:13]1[C:14]2[C:19](=[CH:18][C:17]([F:20])=[C:16]([OH:21])[CH:15]=2)[N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:25])=[O:3])=[CH:6][CH:7]=2)[CH:12]=1)#[N:24]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 58437431HCID 58437431, compound

Product 1

HCID 58437488HCID 58437488, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-cyano-6-fluoro-5-methoxyindol-1-yl)benzoic acid ethyl ester (1.2 g) in dichloromethane (20 mL) was added boron tribromide (1.0 mol/L dichloromethane solution) (10 mL) in a dropwise manner under ice cooling, and this mixture was stirred at room temperature for 12 hours. This reaction mixture was poured into water, and this mixture was extracted with ethyl acetate, concentrated under reduced pressure to give the title compound (0.44 g).

Workup

  1. extractionthis mixture was extracted with ethyl acetate
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-318ed83f4352436b8f413d736e490175
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Reaction notes

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