Triethylamine → 303149-10-2

HRID 1988814Notes

Reaction equation

HRID 1988814 reaction equation
N1C2C(=CC=CC=2)C[C:2]1=[O:10].Br[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])/[C:15]/2=[N:22]\[C:23]1[CH:28]=[CH:27][CH:26]=[C:25](C(F)(F)F)[CH:24]=1.C(N(CC)CC)C.[C:40]1(B(O)O)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:2][O:10][C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:22]=[C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[CH:12][CH:13]=2)[N:17]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:16]1=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 321710OxindoleHCID 178517024HCID 178517024, compound

Product 1

HCID 1471832303149-10-2Yield 20%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

(3Z)-5-BROMO-1-PHENYL-3-{[3-TRIFLUOROMETHYL)PHENYL]IMINO}-1,3-DIHYDRO-2H-INDOL-2-ONE: A mixture of (3Z)-5-bromo-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2H-indol-2-one (100 mg, 0.272 mmol), copper (II) acetate (54 mg, 0.33 mmol), triethylamine (82.8 mg, 0.817 mmol), and benzene boronic acid (40 mg, 0.325 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 (22 mg, 20%).

Workup

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

Sources & evidence

ORD record
ord-9e44cecf254e47918a0a4164db8e181f
Source dataset
uspto-grants-2010_01
Patent number
US07642281B2

Reaction notes

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