5-Bromo-1-indanone → 5-bromo-1-[(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1-trityl-1H-imidazol-2-yl)methyl]indan-1-ol

HRID 425436Notes

Reaction equation

HRID 425436 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=[C:10]([CH2:12][C:13]2([C:16]([F:19])([F:18])[F:17])[CH2:15][CH2:14]2)[N:11]=1.[Br:39][C:40]1[CH:41]=[C:42]2[C:46](=[CH:47][CH:48]=1)[C:45](=[O:49])[CH2:44][CH2:43]2>C1COCC1>[Br:39][C:40]1[CH:41]=[C:42]2[C:46](=[CH:47][CH:48]=1)[C:45]([CH2:6][C:7]1[N:8]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:9]=[C:10]([CH2:12][C:13]3([C:16]([F:17])([F:18])[F:19])[CH2:14][CH2:15]3)[N:11]=1)([OH:49])[CH2:44][CH2:43]2

Participants

5

Reactant 3

HCID 5206955-Bromo-1-indanoneHCID 591620382-Methyl-4-((1-(trifluoromethyl)cyclopropyl)methyl)-1-trityl-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 667056725-bromo-1-[(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1-trityl-1H-imidazol-2-yl)methyl]indan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium (14.8 mL, 23.7 mmol) was added to a solution of 2-methyl-4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1-trityl-1H-imidazole (7.05 g, 15.8 mmol) in THF (30 mL) at −78° C. After 5 min, a solution of 5-bromoindan-1-one (5 g, 23.7 mmol) in THF (2 mL) was added dropwise to the reaction mixture. The solution was stirred at −78° C. for 2 h. The reaction was quenched with the addition of saturated aqueous NH4Cl. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue. The residue was purified by column chromatography eluting with 0-100% EtOAc/hexanes to give 5-bromo-1-[(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1-trityl-1H-imidazol-2-yl)methyl]indan-1-ol.

Workup

  1. customThe reaction was quenched with the addition of saturated aqueous NH4Cl
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a residue
  7. customThe residue was purified by column chromatography
  8. washeluting with 0-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-889b82f1f5bb4e61b0fedcf53faf1c10
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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