Methyl iodide → HCID 69433010, compound

HRID 854386Notes

Reaction equation

HRID 854386 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]=[C:6]2[C:22]1[C:23]2[CH:30]=[C:29]([C:31]3[C:39]4[C:34](=[CH:35][CH:36]=[C:37]([O:40][CH3:41])[CH:38]=4)[NH:33][CH:32]=3)[N:28]([S:42]([C:45]3[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=3)(=[O:44])=[O:43])[C:24]=2[N:25]=[CH:26][N:27]=1.[H-].[Na+].[CH3:54]I>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)(=[O:13])=[O:14])[CH:7]=[C:6]2[C:22]1[C:23]2[CH:30]=[C:29]([C:31]3[C:39]4[C:34](=[CH:35][CH:36]=[C:37]([O:40][CH3:41])[CH:38]=4)[N:33]([CH3:54])[CH:32]=3)[N:28]([S:42]([C:45]3[CH:46]=[CH:47][C:48]([CH3:51])=[CH:49][CH:50]=3)(=[O:44])=[O:43])[C:24]=2[N:25]=[CH:26][N:27]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69431925HCID 69431925, compound

Product 1

HCID 69433010HCID 69433010, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl)-6-(5-methoxy-1H-indol-3-yl)-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine [270 mg, Reference Example 10] in dimethylformamide (10 mL) was added the sodium hydride (10 mg, 60% dispersion in oil) and methyl iodide (0.025 mL) under inert atmosphere. The solution was stirred for 16 hours at room temperature and the solvent was evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (50:50, v/v) to give the title compound (93 mg) as an amorphous solid. MS: 732 [MH]+. LCMS (Method B) RT=4.68 minutes.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate The organic phase
  3. customwas separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (50:50

Sources & evidence

ORD record
ord-75508e74fc9549248b87bd6a9f84c2de
Source dataset
uspto-grants-2007_08
Patent number
US07259154B2

Reaction notes

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