Water → HCID 22032912, compound

HRID 2221277Notes

Reaction equation

HRID 2221277 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)[CH:7]=[CH:8][CH:9]=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1COCC1>[C:19]1([S:25]([N:15]2[C:16]3[C:12](=[CH:11][C:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=4)=[CH:18][CH:17]=3)[CH:13]=[CH:14]2)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 22032967HCID 22032967, compound

Product 1

HCID 22032912HCID 22032912, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred slurry of 0.61 g (12.7 mmol), 50% dispersion of NaH in mineral oil, in 36 mL anhydrous THF was added 2.15 g crude 5-(3-chlorophenyl)indole (Step 1 of Example 45). The solution was allowed to stir at room temperature 15 min upon which time 1.2 mL (9.4 mmol) phenylsulfonyl chloride was added dropwise. The solution was allowed to stir at room temperature overnight and was poured into water and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated. The crude product was chromatographed on SiO2 using 10-25% EtOAc-Hex to afford 1.46 g 1-benzenesulfonyl-5-(3-chlorophenyl)-1H-indole as a tan solid.

Workup

  1. additionwas added dropwise
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on SiO2 using 10-25% EtOAc-Hex

Sources & evidence

ORD record
ord-6c325cfb85a44cfa96c7233eb43acdb3
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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