Sodium Carbonate → HCID 178516709, compound

HRID 218095Notes

Reaction equation

HRID 218095 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[N:8]=[C:9]2\[C:10](=[O:24])[N:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[C:17]\2=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:4][CH:3]=1.[S:25]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26]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:18]1([N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)/[C:9](=[N:8]/[C:5]3[CH:6]=[CH:7][C:2]([C:27]4[CH:28]=[CH:29][S:25][CH:26]=4)=[CH:3][CH:4]=3)/[C:10]2=[O:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 178516704HCID 178516704, compound

Product 1

HCID 178516709HCID 178516709, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3Z)-3-[(4-bromophenyl)imino]-1-phenyl-1,3-dihydro-2H-indol-2-one (50.0 mg, 0.133 mmol), thiophene-3-boronic acid (26.0 mg, 0.199 mmol), tetrakis(triphenylphosphine)palladium(0) (31.0 mg, 0.0268 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 CH7Cl2 (3×1 ml), and concentrated. The crude product was purified by preparative TLC using 10% methanol in CHCl3, giving the desired product (18 mg, 35%).

Workup

  1. concentrationThe crude product was concentrated in vacuo
  2. extractionthe residue was extracted with CH7Cl2 (3×1 ml)
  3. concentrationconcentrated
  4. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-092f3ec519bd486190e5dfd9546d6b39
Source dataset
uspto-grants-2012_06
Patent number
US08198313B2

Reaction notes

Loading…