2-Methylindole → HCID 10126871, compound

HRID 1988145Notes

Reaction equation

HRID 1988145 reaction equation
C([Li])CCC.CC(C)([O-])C.[K+].[CH3:12][C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2.[F:22][C:23]([F:40])([F:39])[C:24](=[O:38])[CH2:25][C:26]([C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[O:36][CH3:37])([CH3:28])[CH3:27]>C(OCC)C>[F:40][C:23]([F:22])([F:39])[C:24]([CH2:12][C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:38])[CH2:25][C:26]([C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[O:36][CH3:37])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 72242-MethylindoleHCID 100849201,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-oneHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

Product 1

HCID 10126871HCID 10126871, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyl lithium (0.673 mL, 1.6 M in hexanes) followed by potassium tert-butoxide (81 mg, 0.718 mmol) was added to a stirred solution of 2-methyl indole (47 mg, 0.359 mmol) in anhydrous diethyl ether (5 mL) at room temperature. Within 5 to 10 minutes, the reaction mixture turned bright orange. 1,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one (100 mg, 0.4 mmol) (Example 1) was then added dropwise as a solution in anhydrous diethyl ether (2 mL). The reaction was quenched with water after 1 hour, extracted with three 5 mL portions of EtOAc, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel affording 45 mg of the title compound as an oil.

Workup

  1. customThe reaction was quenched with water after 1 hour
  2. extractionextracted with three 5 mL portions of EtOAc
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel affording 45 mg of the title compound as an oil

Sources & evidence

ORD record
ord-1e68b8b4f85045cdb6dc93631d55d70b
Source dataset
uspto-grants-2009_06
Patent number
US07553966B2

Reaction notes

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