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

HRID 913405Notes

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][CH3:21])=[O:19].C([O-])([O-])=O.[Cs+].[Cs+]>>[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][CH3:21])=[O:19]

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 60984Methyl bromoacetate

HCID 249856324-chloro-2-(difluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 24985637Methyl [4-chloro-5-cyano-2-(difluoromethyl)-1H-indol-1-yl]acetate

Procedure

Synthesized as described in Example 4 using 4-chloro-2-(difluoromethyl)-1H-indole-5-carbonitrile, methyl bromoacetate (2 eq) and Cs2CO3 (2 eq): MS (ES) m/z 299 (M+1).

Workup

customSynthesized

Sources & evidence

ORD record: ord-a74e537798c94450b14a9b2abc62e73f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026262B2

Reaction notes

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