Sodium Carbonate → HCID 178516715, compound

HRID 218098Notes

Reaction equation

HRID 218098 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6](=[O:17])/[C:5]/2=[N:18]\[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:8]1([N:7]2[C:11]3[C:12](=[CH:13][C:14]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:15][CH:16]=3)/[C:5](=[N:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)/[C:6]2=[O:17])[CH:9]=[CH:10][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 178516714HCID 178516714, compound

Product 1

HCID 178516715HCID 178516715, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
67 °C

Procedure

A mixture of (3z)-5-bromo-1-phenyl-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2H-indol-2-one (22 mg, 0.05 mmol), tetrakis(triphenylphosphine)palladium(0) (12.0 mg, 0.01 mmol), benzene boronic acid (10 mg, 0.08 mmol) in THF (5 mL), and aqueous Na2CO3 (2M, 100 μL) was heated at 67° C. for 24 h. The crude product was concentrated in vacuo and the residue was extracted with CH2Cl2 (3×1 ml), concentrated, and purified by preparative TLC using 10% methanol in CHCl3, giving the desired product (4 mg, 18%).

Workup

  1. concentrationThe crude product was concentrated in vacuo
  2. extractionthe residue was extracted with CH2Cl2 (3×1 ml)
  3. concentrationconcentrated
  4. custompurified by preparative TLC

Sources & evidence

ORD record
ord-4e7f50a8ad5047ccbd87d6c9ebd3084d
Source dataset
uspto-grants-2012_06
Patent number
US08198313B2

Reaction notes

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