Iodoethane → (3-ethoxy-5-ethyl-2-fluorophenyl)(4-phenyl-1-trityl-1H-imidazol-2-yl)methanol

HRID 2105089Notes

Reaction equation

HRID 2105089 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:11]([OH:42])[C:12]2[N:13]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)[C:6]([F:10])=[C:7]([OH:9])[CH:8]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].I[CH2:50][CH3:51]>CN(C=O)C.CCOC(C)=O>[CH2:50]([O:9][C:7]1[C:6]([F:10])=[C:5]([CH:11]([C:12]2[N:13]([C:23]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)[OH:42])[CH:4]=[C:3]([CH2:1][CH3:2])[CH:8]=1)[CH3:51]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 68813439HCID 68813439, compound

Product 1

HCID 68813924(3-ethoxy-5-ethyl-2-fluorophenyl)(4-phenyl-1-trityl-1H-imidazol-2-yl)methanolYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 448.2 (1.00 g, 1.80 mmol) in 10 mL DMF at rt, were added K2CO3 (229 mg, 2.16 mmol) and iodoethane (432 μL, 5.4 mmol). The mixture was stirred at rt for 19 h, then diluted with EtOAc. The organic phase was washed with H2O (2×), sat. Na2SO3 and brine, dried (Na2SO4), filtered through 1″ SiO2 and concentrated to afford 1.05 g of Intermediate 448.3 as a colorless solid. LCMS (2 min gradient) RT=1.92 min, 583.3 (M+H)+.

Workup

  1. washThe organic phase was washed with H2O (2×), sat. Na2SO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered through 1″ SiO2
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f35576a85b4840ee8732191cb68b061d
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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