Methyl iodide → HCID 68443628, compound

HRID 83157Notes

Reaction equation

HRID 83157 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:29]=[CH:28][C:18]([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:20])=[CH:17][N:16]=1.[CH3:30][Si]([N-][Si](C)(C)C)(C)C.[K+].IC>C1COCC1>[CH3:30][N:21]([CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[C:19](=[O:20])[C:18]1[CH:28]=[CH:29][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 575200146-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide

Product 1

HCID 68443628HCID 68443628, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide (200 mg, 0.51 mmol) in THF (2 mL) was added at 0° C. potassium bis(trimethylsilyl)amide (0.91 M in THF, 614 μL, 0.56 mmol) over a period of 2 min. After stirring for 0.5 h at this temperature iodomethane (41 μL, 0.66 mmol) was added and the resulting suspension was stirred for 2 h at ambient temperature. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100) afforded the title compound (91 mg, 44%) as a white foam. MS: m/e=408.5 [M+H]+.

Workup

  1. additionwas added
  2. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100)

Sources & evidence

ORD record
ord-7ebf8d0e3d7e472196c9dba8dc8ae8b0
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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