Pyridine → (S)-Methyl 2-(5-(4-benzamidophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403917Notes

Reaction equation

HRID 403917 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[CH2:11]3)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:32](Br)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:32]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[CH2:11]3)=[CH:4][CH:3]=1)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12056Benzoyl bromideHCID 131731499(S)-Methyl 2-(5-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 131731524(S)-Methyl 2-(5-(4-benzamidophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound of example 223 (100 mg, 0.295 mmol) in dichloromethane (3 mL), pyridine (70.53 mg, 0.885 mmol) was added and stirred for 5 min followed by addition of benzoyl bromide (81.96 mg, 0.443 mmol). The reaction mixture was stirred for about 16 h. After completion of the reaction, the solvent was evaporated to obtain the title compound, which was directly used for the preparation of compound of example 305.

Workup

  1. stirringThe reaction mixture was stirred for about 16 h
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-345f2078548949bebb61431b601d1a2a
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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