Sodium 4-bromobenzene-1-sulfinate → 2-[4-(4-bromo-benzenesulfonylmethyl)-oxazol-2-yl]-5-trifluoromethoxy-1H-indole

HRID 1392235

Reaction equation

HRID 1392235 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=3)[O:6][CH:7]=1.[Na+].[Br:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O-:32])=[O:31])=[CH:26][CH:25]=1>CN(C)C=O>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH2:2][C:3]2[N:4]=[C:5]([C:8]3[NH:9][C:10]4[C:15]([CH:16]=3)=[CH:14][C:13]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=4)[O:6][CH:7]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 23670685Sodium 4-bromobenzene-1-sulfinateHCID 1363319652-(4-chloromethyl-oxazol-2-yl)-5-trifluoromethoxy-1H-indole

Product 1

HCID 1363319632-[4-(4-bromo-benzenesulfonylmethyl)-oxazol-2-yl]-5-trifluoromethoxy-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-chloromethyl-oxazol-2-yl)-5-trifluoromethoxy-1H-indole (0.3 g, 0.95 mmol) and 4-bromo-benzenesulfinic acid sodium salt (0.92 g, 3.8 mmol) in N,N-dimethyl formamide (10 ml) was stirred for 16 h at 60° C. After cooling the mixture was poured on water (20 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Chromatography on silica gel (ethyl acetate/iso-hexanes 1:1) yielded the title compound as tan solid. Yield 0.28 g (59%)

Workup

  1. temperatureAfter cooling the mixture
  2. additionwas poured on water (20 ml)
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49b11a5577a741eeba995e98319a614a
Source dataset
uspto-grants-2008_03
Patent number
US07342030B2

Linked notes

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