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

HRID 251023Notes

Reaction equation

HRID 251023 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-286763f35eb14ef08860dc367c2320a9
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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