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

HRID 251023ノート

反応式

HRID 251023 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 222Ammonia溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-286763f35eb14ef08860dc367c2320a9
出典データセット
uspto-grants-2011_01
特許番号
US07863293B2

反応ノート

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