Methyl iodide → HCID 69055621, compound

HRID 490769Notes

Reaction equation

HRID 490769 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][CH:17]([C:19]1[O:23][C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[N:21][C:20]=1[CH:34]([CH3:36])[CH3:35])[CH3:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].I[CH3:40]>O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:40])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][CH:17]([C:19]1[O:23][C:22]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:28][CH:29]=3)=[N:21][C:20]=1[CH:34]([CH3:35])[CH3:36])[CH3:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69054630HCID 69054630, compound

Product 1

HCID 69055621HCID 69055621, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-{2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propoxy}-1H-indole-2-carboxylic acid ethyl ester (0.117 g, 0.234 mmol) is stirred with sodium hydride, 60% mineral oil (0.011 g, 0.28 mmol) and NN-dimethyl formamide (12 mL). Iodomethane (16 uL, 0.26 mmol) is added and the mixture is stirred at 80 deg C. 2 hr, and room temperature 18 hr. The mixture is diluted with water (50 mL), and the product is extracted into ethyl acetate (2×50 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica gel chromatography eluting with 8:2 hexanes:ethyl acetate to 6:4 hexanes:ethyl acetate to afford the title compound as a tan solid, 0.062 g, 51%). MS M++1 515. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. custom2 hr, and room temperature 18 hr
  2. extractionthe product is extracted into ethyl acetate (2×50 mL)
  3. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via silica gel chromatography
  7. washeluting with 8:2 hexanes

Sources & evidence

ORD record
ord-1a7066fbda164816b8d1394e435bfe3f
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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