Water → 5-chloro-7-fluoro-2-pyridin-3-yl-1H-indole

HRID 1630836노트

반응식

HRID 1630836 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:5]([NH2:16])=[C:4]([F:17])[CH:3]=1.CC(C)([O-])C.[K+].O>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([F:17])[CH:3]=1)[NH:16][C:9]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[CH:8]2

참가 물질

5

반응물 3

HCID 962Water2회HCID 23665647Potassium tert-butoxideHCID 582155984-Chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine

생성물 1

HCID 595346575-chloro-7-fluoro-2-pyridin-3-yl-1H-indole

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a solution of 4-chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine (3.1 g, 12.57 mmol) in NMP (40 mL) is added potassium tert-butoxide (2.1 g, 18.85 mmol) and the mixture is stirred overnight. Water (1 mL) is added to quench the reaction and the mixture is poured into water (100 mL). The mixture is extracted with diethyl ether five times. The combined organic phase is partially concentrated, resulting in precipitation of the product, which is filtered through a glass sintered funnel and washed with dichloromethane to afford 5-chloro-7-fluoro-2-pyridin-3-yl-1H-indole as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.10-7.15 (m, 2H), 7.47-7.53 (m, 2H), 8.31 (dt, J=8.2, 1.9, 1.8 Hz, 1H), 8.55 (d, J=4.3 Hz, 1H), 9.16 (s, 1H), 12.23 (s, 1H).

후처리

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture is extracted with diethyl ether five times
  4. concentrationThe combined organic phase is partially concentrated
  5. customresulting in precipitation of the product, which
  6. filtrationis filtered through a glass sintered funnel
  7. washwashed with dichloromethane

출처 및 근거

ORD 기록
ord-2b7a4759798243a093aa8f887932ae2a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791141B2

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