Methyl iodide → HCID 178441293, compound

HRID 76264Notes

Reaction equation

HRID 76264 reaction equation
[CH2:1]([C:5]1=[CH:6][N:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[S:8]/[C:9]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[CH:14][C:13]=1[OH:20])[CH2:2][CH2:3][CH3:4].[C:26](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.O>[CH2:1]([C:5]1=[CH:6][N:7]([C:22]([CH3:24])([CH3:23])[CH3:25])[S:8]/[C:9]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[CH:14][C:13]=1[O:20][CH3:26])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178441292HCID 178441292, compound

Product 1

HCID 178441293HCID 178441293, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 56A (350 mg, 0.97 mmol) and cesium carbonate (375 mg, 1.94 mmol) in DMF (20 mL) was treated with iodomethane (165 mg, 1.17 mmol). The mixture was stirred at rt for 2 hrs, diluted with H2O and extracted with EtOAc (2×). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 246 mg (68%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 0.99 (t, J=7.36 Hz, 3 H) 1.36-1.51 (m, 2 H) 1.67 (s, 9 H) 1.68-1.78 (m, 2 H) 2.85 (dd, J=7.67 Hz, 2 H) 4.02 (s, 3 H) 7.11 (d, J=8.59 Hz, 1 H) 7.97 (dd, J=8.59, 2.15 Hz, 1 H) 7.96 (s, 1 H) 8.64 (d, J=2.15 Hz, 1 H) 9.96 (s, 1 H); MS (DCI/NH4+) m/z 375 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2fb838d3dc794c08904ea3991fe19894
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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