Methanol → HCID 59024659, compound

HRID 2054117Notes

Reaction equation

HRID 2054117 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH3:7]O.[Br:9][C:10]([F:31])([F:30])[C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19](SC)=[CH:18][CH:17]=2)[C:12]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.O>[Br:9][C:10]([F:30])([F:31])[C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:17]=[CH:18][C:19]([S:3]([CH3:7])(=[O:5])=[O:2])=[CH:20][CH:21]=2)[C:12]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 59024652HCID 59024652, compound

Product 1

HCID 59024659HCID 59024659, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Oxone® (120 mg), H2O (3 mL) and MeOH (1 mL) was added dropwise to a solution of 6 (43 mg, 0.108 mmol) in THF (5 mL) with stirring. The reaction mixture was stirred for 2 h and diluted with H2O (10 mL). The product was extracted with CH2Cl2 and the organic extracts were dried over anhydrous MgSO4. After filtration, the filtrate was concentrated and the resulting residue was purified by flash column chromatography with hexanes-EtOAc (4:1) to give 7 (39 mg, 81%) as a colorless solid: 1H NMR (CDCl3) δ 3.11 (3H, s, SO2Me), 7.27-7.98 (9H, m, Ar). HRMS (FAB) Calculated for C17H13BrF2NO3S (MH+, 427.9766). Found: 427.9765.

Workup

  1. stirringThe reaction mixture was stirred for 2 h
  2. extractionThe product was extracted with CH2Cl2
  3. dry with materialthe organic extracts were dried over anhydrous MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe resulting residue was purified by flash column chromatography with hexanes-EtOAc (4:1)

Sources & evidence

ORD record
ord-db8a4d7723af42588d4975bb7802cd72
Source dataset
uspto-grants-2008_02
Patent number
US07329401B2

Reaction notes

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