Benzenesulfonyl chloride → HCID 11068230, compound

HRID 2370331Notes

Reaction equation

HRID 2370331 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[C:14]2[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8][CH:7]=1)[CH:4]=[CH2:5].[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:3]([C:6]1[C:14]2[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]([S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])[CH:7]=1)[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 66773310HCID 66773310, compound

Product 1

HCID 11068230HCID 11068230, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. cooled suspension of sodium hydride (60% dispersion in mineral oil, 0.450 g, 11.24 mmol) in DMF (50 mL) was slowly added a solution of methyl 3-allyl-1H-indole-4-carboxylate (2.20 g, 10.22 mmol) from Step A above in DMF (30 mL). The mixture stirred at 0° C. under an atmosphere of nitrogen for 1 h. To this was added benzenesulfonyl chloride (1.30 mL, 10.22 mmol). The mixture continued to stir for 16 h while gradually warming to room temperature. The mixture was carefully quenched with saturated aqueous ammonium chloride solution (300 mL) and the aqueous mixture was extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with water (4×100 mL), brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0 to 30% ethyl acetate in hexanes) afforded methyl 3-allyl-1-(phenylsulfonyl)-1H-indole-4-carboxylate (3.15 g, 87%) as a pale yellow oil, which crystallized upon standing: 1H NMR (500 MHz, CDCl3) δ 8.19 (m, 1H), 7.85 (m, 2H), 7.63 (m, 1H), 7.55 (m, 1H), 7.44 (s, 1H), 7.41 (m, 2H), 7.32 (m, 2H), 5.96 (m, 1H), 5.07 (m, 1H), 4.97 (m, 1H), 3.89 (s, 3H), 3.54 (m, 2H): MS (ESI+) m/z 356 (M+H).

Workup

  1. stirringto stir for 16 h
  2. temperaturewhile gradually warming to room temperature
  3. customThe mixture was carefully quenched with saturated aqueous ammonium chloride solution (300 mL)
  4. extractionthe aqueous mixture was extracted with ethyl acetate (3×300 mL)
  5. washThe combined organic layers were washed with water (4×100 mL), brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by column chromatography (silica gel, 0 to 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-82fdeec0a6c04affa7dd51fafc343d73
Source dataset
uspto-grants-2014_04
Patent number
US08710047B2

Reaction notes

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