Water → HCID 58437488, compound

HRID 1258232Notes

Reaction equation

HRID 1258232 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-f4943fb3572045cfa1482b5317ed66e6
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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