Pyridine → HCID 66755963, compound

HRID 1642128Notes

Reaction equation

HRID 1642128 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)=[O:4].N1C=CC=CC=1.[Cl:20][C:21]1[CH:22]=[C:23]([S:28](Cl)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1[Cl:27]>C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23]([S:28]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][CH:5]2[C:3]([O:2][CH3:1])=[O:4])(=[O:29])=[O:30])[CH:24]=[CH:25][C:26]=1[Cl:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 2794655Methyl indoline-2-carboxylate

Product 1

HCID 66755963HCID 66755963, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Indoline-2-carboxylic acid methyl ester (33.0 g, 149.7 mmol) was dissolved in DCM (400 ml), and pyridine (37.8 ml, 463.2 mmol) was added thereto. A solution of 3,4-dichlorobenzenesulfonyl chloride (24.1 ml, 154.4 mmol) dissolved in DCM (100 ml) was then added, and the mixture was stirred overnight under reflux and then cooled to room temperature. The mixture was diluted with DCM and washed in succession with 0.5 M KHSO4, saturated NaHCO3 solution and saturated NaCl solution. The organic phase was dried (sodium sulfate) and concentrated in vacuo.

Workup

  1. additionwas then added
  2. temperatureunder reflux
  3. washwashed in succession with 0.5 M KHSO4, saturated NaHCO3 solution and saturated NaCl solution
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba8822409d5a4b808b9db13602241b29
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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