Ammonia → 4-aminomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 475256Notes

Reaction equation

HRID 475256 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]#[N:17])[C:10]=2[CH:9]=[N:8]1.N>CO.[Ni]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[C:11]([CH2:16][NH2:17])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 71272391HCID 71272391, compound

Product 1

HCID 226611964-aminomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleYield 79%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 198 (430 mg, 1.89 mmol) in a 7N solution of NH3 in MeOH (20 mL) was added Raney nickel (50 mg), and the mixture was stirred under hydrogen (1 atm) at RT overnight. The Raney nickel was removed by filtration. The filtrate was concentrated to afford 340 mg (79%) of (1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl) methanamine (199) as yellow syrup: MS (ESI) m/z=232.2 [M+1]+.

Workup

  1. customThe Raney nickel was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5d1261c659a34763994c07971a5d2b95
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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