Water → 4-(5-Bromo-3-cyanoindol-1-yl)benzoic acid ethyl ester

HRID 73359Notes

Reaction equation

HRID 73359 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]#[N:12].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19]([O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=1)[CH3:20].O>CN(C)C=O>[CH2:19]([O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=3)[C:5]([C:11]#[N:12])=[CH:6]2)=[CH:25][CH:24]=1)[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 36233545-Bromo-3-cyanoindole

Product 1

HCID 250523464-(5-Bromo-3-cyanoindol-1-yl)benzoic acid ethyl esterYield 53.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-3-cyanoindole (2.0 g) in N,N-dimethylformamide (50 mL) were added cesium carbonate (7.4 g) and 4-fluorobenzoic acid ethyl ester (3.0 g), and this mixture was stirred at 80° C. for 48 hours. This reaction mixture was poured into water, and the precipitated solid was collected by filtration. This solid was washed with water, dried under reduced pressure at 50° C. to give the title compound (1.8 g).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThis solid was washed with water
  3. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-7c6ac7a5b851449b93877eb6f92bdebf
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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