Methyl iodide → HCID 89702227, compound

HRID 2202947Notes

Reaction equation

HRID 2202947 reaction equation
[H-].[Na+].[CH:3]1([C:6]2[N:7]=[C:8]3[CH:13]=[CH:12][C:11]([N:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=5)=[CH:16][C:15]4=[O:29])=[CH:10][N:9]3[C:30]=2[CH2:31][OH:32])[CH2:5][CH2:4]1.I[CH3:34]>C1COCC1>[CH:3]1([C:6]2[N:7]=[C:8]3[CH:13]=[CH:12][C:11]([N:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=5)=[CH:16][C:15]4=[O:29])=[CH:10][N:9]3[C:30]=2[CH2:31][O:32][CH3:34])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89690302HCID 89690302, compound

Product 1

HCID 89702227HCID 89702227, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of NaH (40% oil dispersion, 22 mg) in THF (9 ml) was added a solution of 1-(2-cyclopropyl-3-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (100 mg) in THF (1 ml) at 0° C., and then the mixture was allowed to warm to room temperature and stirred for 30 min. Iodomethane (22 pa) in THF (0.5 ml) was added, and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with ice-water and extracted with DCM. The combined DCM layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (MeOH/DCM) followed by recrystallization from DCM/hexane to give the title compound (40 mg) as a white solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 h
  2. customThe reaction mixture was quenched with ice-water
  3. extractionextracted with DCM
  4. washThe combined DCM layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel column chromatography (MeOH/DCM)
  8. customfollowed by recrystallization from DCM/hexane

Sources & evidence

ORD record
ord-cbefd9cf59cf43e891b58a49fc80148b
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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