Pyridine → HCID 11450869, compound

HRID 1642130Notes

Reaction equation

HRID 1642130 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.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>C(Cl)Cl>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([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:30])=[O:29])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 2794655Methyl indoline-2-carboxylate

Product 1

HCID 11450869HCID 11450869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Indoline-2-carboxylic acid methyl ester (32.7 g, 151.8 mmol) was dissolved in DCM (400 ml), and pyridine (37.4 ml, 459.0 mmol) was added thereto. A solution of 4-methoxybenzenesulfonyl chloride (31.6 g, 153 mmol) dissolved in DCM (100 ml) was then added, and stirring was carried out overnight at 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. The residue was purified by column chromatography on silica gel (heptane/ethyl acetate 2:1).

Workup

  1. additionwas then added
  2. washwashed in succession with 0.5 M KHSO4, saturated NaHCO3 solution and saturated NaCl solution
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (heptane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-c294b27fcbd340a88ec9f98f5c1f685f
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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