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Lithium diisopropylamide → (4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)methanol

HRID 2105025
Notes
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Reaction equation

HRID 2105025 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][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.C([N-]C(C)C)(C)C.[Li+].[Si:40]([O:47][C:48]1[C:49]([F:58])=[C:50]([CH:53]=[C:54]([CH2:56][CH3:57])[CH:55]=1)[CH:51]=[O:52])([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH:51]([C:50]2[CH:53]=[C:54]([CH2:56][CH3:57])[CH:55]=[C:48]([O:47][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[C:49]=2[F:58])[OH:52])[N:11]([C:13]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 221851434-(2-bromophenyl)-1-trityl-1H-imidazoleHCID 598380723-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde

Product 1

HCID 68815662(4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)methanolYield 54.1%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
0 °C

Procedure

To a solution of Intermediate 217.1 (650 mg, 1.40 mmol) in 10 mL THF at 0° C., was added a solution of lithium diisopropylamide (2M in heptane/THF/ethylbenzene, 0838 mL, 1.68 mmol). The mixture was stirred at 0° C. for 30 min, then a solution of Intermediate 188.3 (356 mg, 1.26 mmol) in 2 mL THF. The mixture was stirred at 0° C. for 2 h, then was quenched with sat. NH4Cl and diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 510 mg of Intermediate 217.2 as a pale yellow solid. LCMS (50 to 100% B, 4 min gradient, A=95% H2O/5% CH3CN/0.1% TFA, B=5% H2O/95% CH3CN/0.1% TFA) RT=5.61 min, 747.67 (M+H)+.

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 h
  2. customwas quenched with sat. NH4Cl
  3. additiondiluted with EtOAc
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-acad0d528b6945de8eb0136a07900e16
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576098B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes