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 1515711ノート

反応式

HRID 1515711 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1eedfd62bab647f6b2c4d700b1ca5051
出典データセット
uspto-grants-2012_07
特許番号
US08222416B2

反応ノート

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