Methyl iodide → HCID 66668993, compound

HRID 1617996Notes

Reaction equation

HRID 1617996 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[CH3:28])[CH2:11][C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=2)=[O:13])=[CH:6][CH:5]=1.I[CH3:30]>O1CCCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[CH3:28])[CH:11]([CH3:30])[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=2)=[O:13])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66666343HCID 66666343, compound

Product 1

HCID 66668993HCID 66668993, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 23 mg, 0.54 mmol) was added to a solution of (R)-3-(4-bromophenyl)-3-(4-chloro-2-methylphenyl)-1-(2-methylpyridin-4-yl)propan-1-one (example 282, step 1; 208 mg, 0.49 mmol) in tetrahydrofuran (7 mL), then after 90 min the reaction mixture was cooled to 0° C. and treated with iodomethane (73 mg, 0.54 mmol). The ice bath was removed, then after 2 h the reaction mixture was partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate 1:1) produced the title compound (149 mg, 70%). Light yellow oil, MS (ESI+): m/z=442.3 ([M+H]+).

Workup

  1. customThe ice bath was removed
  2. customafter 2 h the reaction mixture was partitioned between sat. aq. ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d63af499aa21459fa56ec707088f5ced
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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