N-tert-butyl-4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-benzamide → N-tert-butyl-4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzamide

HRID 1515711노트

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HRID 1515711 반응식
[C:1]([NH:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:20]2[NH:29][C:23]3=[N:24][CH:25]=[C:26]([F:28])[CH:27]=[C:22]3[CH:21]=2)=[CH:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([NH:5][C:6](=[O:30])[C:7]1[CH:8]=[CH:9][C:10]([CH:13]([C:20]2[NH:29][C:23]3=[N:24][CH:25]=[C:26]([F:28])[CH:27]=[C:22]3[CH:21]=2)[CH2:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 1

HCID 67229020N-tert-butyl-4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-benzamide

생성물 1

HCID 67228592N-tert-butyl-4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzamide수율 91.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

A mixture of N-tert-butyl-4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-benzamide (380 mg, 0.938 mmol) and 10% palladium on activated carbon (100 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 6 h. The mixture was cooled to room temperature. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford N-tert-butyl-4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzamide (350 mg, 91.9%) as a white solid: LC/MS m/e calcd for C25H30FN3O [M+H]+ 408.54, observed 408.1.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customThe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-1eedfd62bab647f6b2c4d700b1ca5051
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222416B2

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