Methyl iodide → HCID 11998804, compound

HRID 1364102Notes

Reaction equation

HRID 1364102 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:26][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH:11]3[CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[S:9][C:5]=2[C:4](=[O:27])[CH2:3]1.[H-].[Na+].[CH3:31]I>CN(C=O)C>[CH3:1][C:2]1([CH3:28])[CH2:26][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH:11]3[CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH3:31])[CH:18]=3)[S:9][C:5]=2[C:4](=[O:27])[CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11998691HCID 11998691, compound

Product 1

HCID 11998804HCID 11998804, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of Example 24 (0.10 g, 0.25 mmol) in DMF (5 mL) at 0° C. was added sodium hydride (0.01 g, 40% dispersion in oil, 0.28 mmol). After stirring at this temperature for 10 minutes, methyl iodide (0.02 mL, 0.28 mmol) was added. The reaction was stirred at r.t. for 1 h and then quenched by the addition of ice. The reaction mixture was then partitioned between EtOAc (15 mL) and water (10 mL) and the organic phase was dried over MgSO4 and concentrated in vacuo. Purification by column chromatography (SiO2, 1:1 EtOAc/hexanes) gave the title compound (0.08 g, 79%) as a white solid. δH (CDCl3) 7.79 (1H, d, J 7.7 Hz), 7.09-7.24 (3H, m), 6.90 (1H, s), 4.05 (2H, m), 3.82 (1H, d, J 12.0 Hz), 3.79 (1H, bs), 3.68 (3H, s), 3.57 (2H, m), 3.41 (2H, m), 2.95 (1H, m), 2.67 (2H, s), 2.34 (2H, s), 1.11 (6H, s). LCMS (ES+) 410.0 (M+H)+.

Workup

  1. stirringThe reaction was stirred at r.t. for 1 h
  2. customquenched by the addition of ice
  3. customThe reaction mixture was then partitioned between EtOAc (15 mL) and water (10 mL)
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by column chromatography (SiO2, 1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-e3e7802b1a2d43118b100da6fc9300aa
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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