Cesium carbonate → 2-[4-Chloro-5-cyano-2-(difluoromethyl)-1H-indol-1-yl]propanamide

HRID 913407Notes

Reaction equation

HRID 913407 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[CH:17]([CH3:21])[C:18]([NH2:20])=[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[CH:17]([CH3:21])[C:18]([NH2:20])=[O:19]

Participants

4

Reactant 3

HCID 10796Cesium carbonate2×HCID 1011182-Bromopropanamide2×HCID 249856324-chloro-2-(difluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 249858052-[4-Chloro-5-cyano-2-(difluoromethyl)-1H-indol-1-yl]propanamide

Conditions

Temperature
90 °C

Procedure

Synthesized as described in Example 4 using 4-chloro-2-(difluoromethyl)-1H-indole-5-carbonitrile, 2-bromo-propionamide (2 eq) and Cs2CO3 (2 eq). After heating at 90° C. for 4 h, additional 2-bromo-propionamide (2 eq) and Cs2CO3 (2 eq) were added and the reaction mixture heated at 110° C. for 15 h: MS (ES) m/z 298 (M+1).

Workup

  1. customSynthesized
  2. temperaturethe reaction mixture heated at 110° C. for 15 h

Sources & evidence

ORD record
ord-615baa6b5e3d4f3482bd33eadea97978
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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