Cesium carbonate → 1-(2-cyanoethyl)-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 913526노트

반응식

HRID 913526 반응식
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]([F:14])([F:13])[F:12])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=2.Br[CH:18]([CH3:21])[C:19]#[N:20].C([O-])([O-])=O.[Cs+].[Cs+]>>[C:19]([CH:18]([N:3]1[C:4]2[C:9](=[C:8]([C:11]([F:12])([F:14])[F:13])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1])[CH3:21])#[N:20].[C:19]([CH2:18][CH2:21][N:3]1[C:4]2[C:9](=[C:8]([C:11]([F:12])([F:14])[F:13])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1])#[N:20]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 1405382-BromopropionitrileHCID 533093462-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

생성물 2

HCID 578001521-(1-cyanoethyl)-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile수율 27%HCID 578004451-(2-cyanoethyl)-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile수율 35%

반응 조건

온도
90 °C

실험 절차

Synthesized as described in Example 23 using 2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile, 2-bromopropionitrile (2 eq) and Cs2CO3 (2 eq) with heating at 90° C. for 30 min. After aqueous workup, purification by flash chromatography afforded 1-(1-cyanoethyl)-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.033 g, 27% yield) (MS (ES) m/z 278 (M+1)) and 1-(2-cyanoethyl)-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.043 g, 35% yield) (MS (ES) m/z 278 (M+1).

후처리

  1. customSynthesized
  2. customAfter aqueous workup, purification by flash chromatography

출처 및 근거

ORD 기록
ord-4d45fa1efc624b8f9dac34c75c4fabd3
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026262B2

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