Triethylamine → HCID 178460609, compound

HRID 1433206Notes

Reaction equation

HRID 1433206 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24](=[O:27])[CH2:25][CH3:26])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1.FC(F)(F)S(O[Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[C:41]([Si:38]([CH3:40])([CH3:39])[O:27][C:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16]1[CH:15]=[CH:14][C:12]2[NH:13][C:9]([CH2:8][O:7][C:6]3[CH:28]=[CH:29][C:3]([C:2]([F:1])([F:30])[F:31])=[CH:4][CH:5]=3)=[N:10][C:11]=2[CH:17]=1)=[CH:25][CH3:26])([CH3:44])([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 178458280HCID 178458280, compound

Product 1

HCID 178460609HCID 178460609, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-propan-1-one (0.073 g, 0.172 mmol) in CH2Cl2 (4 mL)) at 0° C. was added tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf) (0.109 g, 0.413 mmol) and triethylamine (0.07 mL, 0.516 mmol). After stirring for 2 hours, the reaction mixture was concentrated, and the residue was purified by chromatography (silica, hexanes: EtOAc, 4:1) to afford the title compound as a yellow oil (0.065 g, 86%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (silica, hexanes: EtOAc, 4:1)

Sources & evidence

ORD record
ord-31e89db5b45c4293b8e75e93979f896b
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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