Triethylamine → HCID 178516716, compound

HRID 218100Notes

Reaction equation

HRID 218100 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5](/[N:9]=[C:10]2\[C:11](=[O:19])[NH:12][C:13]3[C:18]\2=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[Br:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)/[C:10](=[N:9]/[C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:4]=3)/[C:11]2=[O:19])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79599(4-Bromophenyl)boronic acidHCID 178517102HCID 178517102, compound

Product 1

HCID 178516716HCID 178516716, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (3Z)-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2H-indol-2-one (100 mg, 0.344 mmol), copper (II) acetate (93 mg, 0.516 mmol), triethylamine (105 mg, 1.03 mmol), and 4-bromobenzene boronic acid (104 mg, 0.516 mmol) in 5 mL of CH2Cl2 was stirred at room temperature for 12 h. The crude mixture was concentrated in vacuo and purified by preparative TLC using EtOAc:hexane (3:7, 1% triethylamine), giving the desired product (65 mg, 42%).

Workup

  1. concentrationThe crude mixture was concentrated in vacuo
  2. custompurified by preparative TLC

Sources & evidence

ORD record
ord-fddc6a31a34446fda534afb135d4e50e
Source dataset
uspto-grants-2012_06
Patent number
US08198313B2

Reaction notes

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