Methyl iodide → HCID 66665072, compound

HRID 872315Notes

Reaction equation

HRID 872315 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][N:21]4[C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:38]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23]([CH2:26][O:27][CH3:38])=[CH:22][N:21]4[C:28]=3[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66665868HCID 66665868, compound

Product 1

HCID 66665072HCID 66665072, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of {1-[4-(6-hydroxymethyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (67 mg) in DMF (0.6 mL) under argon at 0° C. was treated with sodium hydride (8.4 mg of a 60% dispersion in mineral oil) and stirred for 30 minutes. Methyl iodide (0.007 mL) was added dropwise, the mixture warmed to rt and stirred for 3 hours. The mixture was partitioned between ethyl acetate and water and the organic phase washed with brine, dried and concentrated in vacuo to give the crude title compound which was used in the next step without further purification.

Workup

  1. stirringstirred for 3 hours
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washthe organic phase washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f3d585d356a4c5eb9848c45690b7a31
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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