Triethylamine → HCID 178477196, compound

HRID 1433214Notes

Reaction equation

HRID 1433214 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:28]=[CH:27][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:26])[CH3:25])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1.FC(F)(F)S(O[Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[C:40]([Si:37]([CH3:39])([CH3:38])[O:26][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:27]=[CH:28][C:3]([C:2]([F:1])([F:29])[F:30])=[CH:4][CH:5]=3)=[N:10][C:11]=2[CH:17]=1)=[CH2:25])([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 1784661661-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-ethanone

Product 1

HCID 178477196HCID 178477196, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-ethanone (0.215 g, 0.524 mmol) in CH2Cl2 (8 mL) at 0° C. was added tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf) (0.304 g, 1.15 mmol) and triethylamine (0.29 mL, 2.10 mmol). After stirring 2 h, the reaction mixture was concentrated, and the residue was purified by chromatography (silica, hexanes: EtOAc, 2:1) to afford the title compound as a yellow oil (0.242 g, 88%).

Workup

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

Sources & evidence

ORD record
ord-fe97730aef5c48a2bf7bdf6808b9b4c5
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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