Benzenesulfonyl chloride → Methyl 1-(Phenylsulfonyl)indoline-5-carboxylate

HRID 84186Notes

Reaction equation

HRID 84186 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH2:9][CH2:8]2)=[O:4].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:22])=[O:21])[CH2:9][CH2:8]2)=[O:4]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 21782110methyl 2,3-dihydro-1H-indole-5-carboxylate

Product 1

HCID 31756086Methyl 1-(Phenylsulfonyl)indoline-5-carboxylateYield 79.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 10 (0.28 g, 1.58 mmol) in pyridine (2 mL), benzenesulfonyl chloride (0.40 ml, 3.16 mmol) was added. The reaction mixture was refluxed overnight. The mixture was then purified by silica gel chromatography (EtOAc:n-hexane=1:3) to afford 11 (0.40 g). 1H NMR (500 MHz, CDCl3): δ 2.99 (t, J=8.6 Hz, 2H), 3.87 (s, 3H), 3.97 (t, J=8.6 Hz, 2H), 7.45-7.48 (m, 2H), 7.56-7.59 (m, 1H), 7.66 (d, J=8.5 Hz, 1H), 7.75 (s, 1H), 7.82 (d, J=7.7 Hz, 2H), 7.90 (d, J=7.9 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe mixture was then purified by silica gel chromatography (EtOAc:n-hexane=1:3)

Sources & evidence

ORD record
ord-e17eed0756ca4c2090bb49cc71ff4a39
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Reaction notes

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