Tetrabutylammonium Fluoride → 3-((4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(hydroxy)methyl)-5-ethyl-2-fluorophenol

HRID 2105026Notes

Reaction equation

HRID 2105026 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH:32]([C:34]2[CH:39]=[C:38]([CH2:40][CH3:41])[CH:37]=[C:36]([O:42][Si](C(C)(C)C)(C)C)[C:35]=2[F:50])[OH:33])[N:11]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH:32]([OH:33])[C:34]2[C:35]([F:50])=[C:36]([OH:42])[CH:37]=[C:38]([CH2:40][CH3:41])[CH:39]=2)[N:11]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68815662(4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)methanol

Product 1

HCID 688172843-((4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(hydroxy)methyl)-5-ethyl-2-fluorophenol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of intermediate 217.2 (500 mg, 0.669 mmol) in 5 mL THF at rt, was added TBAF (1M in THF, 0.669 mL, 0.669 mmol). The mixture was stirred at rt for 30 min. The mixture was diluted with EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was triturated with hexanes (10 mL) to afford 3-((4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(hydroxy)methyl)-5-ethyl-2-fluorophenol. To a solution of this product in 5 mL DMF at rt, were added K2CO3 (111 mg, 0.803 mmol) and iodoethane (161 μL, 2.01 mmol). The mixture was stirred at rt for 15 h, then diluted with EtOAc. The organic phase was washed with H2O (2×), sat. Na2SO3 and brine, dried (Na2SO4), filtered through a 1″ pad of silica gel and concentrated to afford 433 mg of Intermediate 217.3 as an off-white solid.

Workup

  1. washwashed with H2O (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was triturated with hexanes (10 mL)

Sources & evidence

ORD record
ord-5f20e6962c2c40c5bc158df3a2ad71bf
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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