Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → HCID 76567949, compound

HRID 1728217Notes

Reaction equation

HRID 1728217 reaction equation
[Br:1][C:2]([CH:4]=[N:5][C:6]([O:8][Si](C)(C)C)=[CH2:7])=[CH2:3].C(OC([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:29])[CH:27]=2)/[C:22](=[CH:30]/[C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)/[C:21]1=[O:38])=O)(C)(C)C>C1(C)C=CC=CC=1>[Br:1][C:2]([CH:4]1[C:22]2([C:23]3[C:28](=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[NH:20][C:21]2=[O:38])[CH:30]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)[CH2:8][C:6](=[O:7])[NH:5]1)=[CH2:3]

Participants

4

Reactant 2

HCID 66640668Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl esterHCID 76567924HCID 76567924, compound

Product 1

HCID 76567949HCID 76567949, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a toluene solution of 1-(1-bromo-vinyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene in toluene (1 M, 37 mL, 37 mmol) was added E/Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester prepared in Example 24a (2.8 g, 7.2 mmol). The reaction mixture was refluxed overnight under argon protection and purified by Prep-HPLC to give product as a white solid (120 mg, 7%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight under argon protection
  2. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-81d6a585840647d5995a224bd4647741
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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