Ammonium formate → 2-Methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 331767Notes

Reaction equation

HRID 331767 reaction equation
Br[C:2]1[C:3]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])=[N:4][C:5]([CH3:17])=[C:6]([CH:16]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:8].C([O-])=O.[NH4+]>CO.C1COCC1.[Pd]>[CH3:17][C:5]1[N:4]=[C:3]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:2]=[CH:16][C:6]=1[C:7]([NH:9][CH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)=[O:8]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 68444456HCID 68444456, compound

Product 1

HCID 684453522-Methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamideYield 20%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-2-methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide (150 mg, 0.37 mmol) in methanol (3 mL) and THF (3 mL) was added under an argon atmosphere palladium on charcoal (10%, 20 mg) and ammonium formate (70 mg, 1.12 mmol). The reaction mixture was stirred for 6 h at ambient temperature. Filtration over Hyflo® and washing with THF afforded the title compound (29 mg, 20%) which was obtained as a light brown semi-solid. MS: m/e=408.3 [M+H]+.

Workup

  1. filtrationFiltration over Hyflo®
  2. washwashing with THF

Sources & evidence

ORD record
ord-67774730b1b7415d96c255528c9ca8e3
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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