Methyl iodide → HCID 67153147, compound

HRID 2390853Notes

Reaction equation

HRID 2390853 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:5]([O:21][CH3:22])=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[CH2:19][OH:20])[CH:7]=1.[H-].[Na+].[CH3:29]I>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[CH2:19][O:20][CH3:29])[C:5]([O:21][CH3:22])=[C:4]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67153077HCID 67153077, compound

Product 1

HCID 67153147HCID 67153147, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

step 2—To a solution of 312 (116 mg, 0.276 mmol) in DMF (5 mL) was added sodium hydride (0.022, 0.550 mmol, 60% mineral oil dispersion). After 20 min, methyl iodide (0.040 mL, 0.643 mmol) was added and the resulting suspension was stirred overnight. The reaction mixture was diluted with EtOAc, thrice washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (5% to 15% EtOAc) to afford 81 mg (68%) of 5-bromo-1-tert-butyl-2-methoxy-3-[(E)-2-(2-methoxymethyl-4-nitro-phenyl)-vinyl]-benzene (314) as an orange oil.

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with an EtOAc/hexane gradient (5% to 15% EtOAc)

Sources & evidence

ORD record
ord-69753d2b59a44aeb832c00a48d41186b
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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