HCID 71272190, compound → HCID 71272687, compound

HRID 475153Notes

Reaction equation

HRID 475153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:18]#[N:19])[C:5]2[C:6]([CH3:17])=[N:7][N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:9]=2[CH:10]=1>[Ni].N.CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:17])=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([CH2:18][NH2:19])[CH:3]=1

Participants

4

Reactant 1

HCID 71272190HCID 71272190, compound

Product 1

HCID 71272687HCID 71272687, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of 6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (150 mg, 0.545 mmol) and Raney nickel (20 mg) in NH3/MeOH (7 N, 10 mL) was stirred under hydrogen at RT overnight. The reaction mixture was filtered through Celite® and the filtrate concentrated to afford (6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamine (123) as an oil (130 mg, 72.3%). MS (ESI): m/z=280 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-59374d6d83d9455a82fea422829b9293
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…