Tetrahydrofuran → 6-(methylsulfonyl)-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

HRID 1987090Notes

Reaction equation

HRID 1987090 reaction equation
CS[C:3]1[C:8]2[C:9](=[O:24])[C:10]3[C:11]([CH:22]=[CH:23][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[N:12][CH:13]=[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:15]=3.O[O:26][S:27]([O-:29])=O.[K+].[CH2:31]1COCC1>CO>[CH3:31][S:27]([C:3]1[C:8]2[C:9](=[O:24])[C:10]3[C:11]([CH:22]=[CH:23][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[N:12][CH:13]=[C:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:15]=3)(=[O:29])=[O:26]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 15980823HCID 15980823, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 159808246-(methylsulfonyl)-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 6-(methylthio)-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (7.4 mg, 0.022 mmol) in THF (0.7 mL) and MeOH (0.2 mL) was added oxone (0.3 mL, 0.138 M in water). The mixture was then stirred at room temperature. After 2 hours, the reaction mixture was concentrated to dryness. The crude residue was diluted with EtOAc and washed with brine. The organic layer was dried over sodium sulfate, filtered, concentrated and purified by reverse phase HPLC (30-100% acetonitrile/water gradient, 0.1% trifluoroacetic acid modifier) to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 9.10 (d, 1H), 8.40 (d, 1H), 8.26 (d, 1H), 8.00 (d, 1H), 7.85 (t, 1H), 7.75 (d, 2H), 7.53 (t, 2H), 7.47 (m, 2H), 7.38 (d, 1H), 3.52 (s, 3H). LRMS (APCI) calculated for C21H16NO3S [M+H]+, 362.0; found 362.1

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. additionThe crude residue was diluted with EtOAc
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by reverse phase HPLC (30-100% acetonitrile/water gradient, 0.1% trifluoroacetic acid modifier)

Sources & evidence

ORD record
ord-83b7abcdb98a42efbb8da8de532c4927
Source dataset
uspto-grants-2009_06
Patent number
US07550478B2

Reaction notes

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