Methanol → HCID 58573342, compound

HRID 931943Notes

Reaction equation

HRID 931943 reaction equation
[Br:1][C:2]1([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[CH3:26]O>S(=O)(=O)(O)O>[Br:1][C:2]1([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH2:14][CH2:15][C:16]([O:18][CH3:26])=[O:17])[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12]

Participants

4

Reactant 2

HCID 887MethanolHCID 58573690HCID 58573690, compound

Product 1

HCID 58573342HCID 58573342, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 4-(3-bromo-6-chloro-2-oxoindolin-3-yl)-4-(3-chlorophenyl)butanoic acid (Example 62, Step E) (5.38 g, 12.14 mmol) in MeOH (120 mL) at room temperature was added one drop of concentrated sulfuric acid. The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: 0 to 50% EtOAc in hexanes) to give the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel (eluent: 0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-54120d6bd6e94e3a9d06d32bee70e3c9
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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