Iodoethane → (5,6-Dimethyl-1-trityl-1h-benzo[d]imidazol-2-yl)(3-ethoxy-5-ethyl-2-fluorophenyl)methanol

HRID 2105081Notes

Reaction equation

HRID 2105081 reaction equation
[CH3:1][C:2]1[C:41]([CH3:42])=[CH:40][C:5]2[N:6]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7]([CH:9]([OH:20])[C:10]3[C:11]([F:19])=[C:12]([OH:18])[CH:13]=[C:14]([CH2:16][CH3:17])[CH:15]=3)=[N:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:50][CH3:51]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[C:41]([CH3:42])=[CH:40][C:5]2[N:6]([C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7]([CH:9]([C:10]3[CH:15]=[C:14]([CH2:16][CH3:17])[CH:13]=[C:12]([O:18][CH2:50][CH3:51])[C:11]=3[F:19])[OH:20])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 688148643-((5,6-dimethyl-1-trityl-1H-benzo[d]imidazol-2-yl)(hydroxy)methyl)-5-ethyl-2-fluorophenol

Product 1

HCID 68815244(5,6-Dimethyl-1-trityl-1h-benzo[d]imidazol-2-yl)(3-ethoxy-5-ethyl-2-fluorophenyl)methanolYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of this phenol (34 mg, 0.061 mmol) in 2 mL DMF, were added K2CO3 (10 mg, 0.073 mmol) and iodoethane (15 μL, 0.18 mmol). The mixture was stirred at rt for 16 h, then was diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered through a 1″ pad of silica gel and concentrated to afford 35.7 mg of Intermediate 415.3. LCMS (2 min gradient) RT=1.97 min, 585.47 (M+H)+.

Workup

  1. washThe organic phase was washed with H2O and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered through a 1″ pad of silica gel
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb06e7e8fbc249b6be97c98700115e6b
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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