Cesium carbonate → 1,1-Dimethylethyl [4-chloro-5-cyano-2-(difluoromethyl)-1H-indol-1-yl]acetate

HRID 1188340Notes

Reaction equation

HRID 1188340 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:13]([F:15])[F:14])[NH:6]2.Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:13]([F:14])[F:15])[N:6]2[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 249856324-chloro-2-(difluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 578001631,1-Dimethylethyl [4-chloro-5-cyano-2-(difluoromethyl)-1H-indol-1-yl]acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized as described in Example 4 using 4-chloro-2-(difluoromethyl)-1H-indole-5-carbonitrile, t-butyl bromoacetate (1.5 eq) and Cs2CO3 (1.5 eq) with MeCN as the solvent (in a sealed tube): MS (ES) m/z 341 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-2f2dd4aaf6464a4cbbee3a716d015c32
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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