1-Methyl-3-(trifluoroacetyl)-1H-indole → HCID 59437212, compound

HRID 244465

Reaction equation

HRID 244465 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]2[N:6]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:7](=[O:10])[N:8]([CH3:9])[C:4]=2[CH:3]=1.C([Li])(C)(C)C.[F:25][C:26]([F:40])([F:39])[C:27]([C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([CH3:38])[CH:30]=1)=[O:28]>C1COCC1>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:6]2[C:5]3[CH:18]=[CH:19][C:2]([C:27]([OH:28])([C:29]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]([CH3:38])[CH:30]=4)[C:26]([F:25])([F:40])[F:39])=[CH:3][C:4]=3[N:8]([CH3:9])[C:7]2=[O:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 35243881-Methyl-3-(trifluoroacetyl)-1H-indoleHCID 594372865-Bromo-1-(4-fluorophenyl)-3-methyl-1,3-dihydro-benzimidazol-2-oneHCID 178418306HCID 178418306, compound

Product 1

HCID 59437212HCID 59437212, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (−78° C.) solution of 5-bromo-1-(4-fluorophenyl)-3-methyl-1,3-dihydro-benzimidazol-2-one (80 mg, 0.25 mmol) in anhydrous THF (3 mL) was added tert-butyllithium (0.2 mL of 1.7 M solution in heptane, 0.34 mmol). After 1 minute, a chilled (−78° C.) solution of 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethanone (57 mg, 0.25 mmol) in anhydrous THF (1 mL) was added. After 10 minutes, the mixture was quenched with ammonium chloride solution and extracted with three 15 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a brownish oil. The residue was purified by column chromatography over silica gel eluting with 0-10% ethyl acetate in methylene chloride to afford 15 mg of the title compound as a white powder. MS m/z 470 (MH+).

Workup

  1. additionwas added
  2. waitAfter 10 minutes
  3. customthe mixture was quenched with ammonium chloride solution
  4. extractionextracted with three 15 mL portions of methylene chloride
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a brownish oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-10% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-b80428248671469ab8751842b05dafcb
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Linked notes

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