1,5,6,7-Tetrahydro-4H-indol-4-one → HCID 60026304, compound

HRID 400692Notes

Reaction equation

HRID 400692 reaction equation
[CH3:1][C:2]([C:12]1[C:20]2[O:19][CH2:18][CH2:17][C:16]=2[CH:15]=[C:14]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:13]=1)([CH3:11])[CH2:3][C:4]1([C:7]([F:10])([F:9])[F:8])[CH2:6][O:5]1.[NH:25]1[C:33]2[CH2:32][CH2:31][CH2:30][C:29](=[O:34])[C:28]=2[CH:27]=[CH:26]1.[O-]CC.[Na+]>C(O)C.C(OCC)(=O)C>[OH:5][C:4]([C:7]([F:9])([F:8])[F:10])([CH2:3][C:2]([C:12]1[C:20]2[O:19][CH2:18][CH2:17][C:16]=2[CH:15]=[C:14]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:13]=1)([CH3:11])[CH3:1])[CH2:6][N:25]1[C:33]2[CH2:32][CH2:31][CH2:30][C:29](=[O:34])[C:28]=2[CH:27]=[CH:26]1

Participants

6

Reactant 3

HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 2723922Sodium ethoxideHCID 57809800HCID 57809800, compound

Product 1

HCID 60026304HCID 60026304, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-5-methanesulfonyl-2,3-dihydrobenzofuran (101 mg, 0.33 mmol) and 1,5,6,7-tetrahydroindol-4-one (74.9 mg, 0.56 mmol) in 0.75 mL of anhydrous ethanol was added sodium ethoxide (21 wt. % solution in ethanol, 103 μL). After heating at 85° C. for 16 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 50% to 60% ethyl acetate-hexanes) to give 80.0 mg (58% yield) of the title compound as a white solid, m.p. 207° C.-208° C.

Workup

  1. dry with materialdried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography with silica gel (eluted with 50% to 60% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-12c7a7db30cc441eaf0a68e5e825fbf3
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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