3-Indol-1-yl-pyridine-2-carbonitrile → C-(3-Indol-1-yl-pyridin-2-yl)-methylamine

HRID 1592453노트

반응식

HRID 1592453 반응식
[N:1]1([C:10]2[C:11]([C:16]#[N:17])=[N:12][CH:13]=[CH:14][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1>N.[Ni]>[N:1]1([C:10]2[C:11]([CH2:16][NH2:17])=[N:12][CH:13]=[CH:14][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

4

반응물 1

HCID 672717063-Indol-1-yl-pyridine-2-carbonitrile

생성물 1

HCID 67273298C-(3-Indol-1-yl-pyridin-2-yl)-methylamine수율 57.3%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 222Ammonia용매

실험 절차

A mixture of 3-indol-1-yl-pyridine-2-carbonitrile (164 mg, 0.75 mmol) in NH3 saturated MeOH (6 mL) was treated with Raney nickel (0.25 g), and placed under 40 psi H2 on a Parr shaker, for 4 h. The mixture was filtered through celite and the cake was washed with methanol. The eluant was concentrated under reduced pressure. Purification of the crude material by column chromatography on silica gel (CH2Cl2-MeOH, 96:4 then 9:1) provided 96 mg (57%) of C-(3-Indol-1-yl-pyridin-2-yl)-methylamine as a clear oil. 1H NMR (CDCl3) δ 1.65 (br s, 2H), 3.72 (s, 2H), 6.73 (d, 1H, J=3.3 Hz), 6.95-7.03 (m, 1H), 7.16-7.21 (m, 3H), 7.38 (dd, 1H, J=9, 6 Hz), 7.66-7.71 (m, 2H), 8.71 (d, 1H, J=4.5 Hz).

후처리

  1. filtrationThe mixture was filtered through celite
  2. washthe cake was washed with methanol
  3. concentrationThe eluant was concentrated under reduced pressure
  4. customPurification of the crude material by column chromatography on silica gel (CH2Cl2-MeOH, 96:4

출처 및 근거

ORD 기록
ord-71a38ec8a0e84dd88c97f26cf2035743
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291631B2

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