Potassium Phosphate, Tribasic → HCID 118324068, compound

HRID 1778287Notes

Reaction equation

HRID 1778287 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[CH:10]=2)[NH:5][C:4](=[O:25])[CH:3]=1.[CH:26](/B(O)O)=[CH:27]\[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH:12]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)[C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][C:4](=[O:25])[CH:3]=[C:2]3/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:19][CH:20]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, Tribasic2×HCID 5702628Styrylboronic acid2×HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl2×HCID 1183240034-bromo-6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinolin-2(1H)-one

Product 1

HCID 118324068HCID 118324068, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalyst2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Bromo-6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinolin-2(1H)-one (50 mg, 0.116 mol, 1 equip), trans-beta-styreneboronic acid (35 mg, 0.232 mmol, 2 equip), SPhos (9.7 mg, 0.023 mmol, 0.2 equip), tripotassium phosphate (49.2 mg, 0.232 mmol, 2 equip), and palladium acetate (2.6 mg, 0.012 mmol, 0.1 equip) were added to 1,4-dioxane (5 mL) and the resulting mixture stirred for 2 h. Additional trans-beta-styreneboronic acid (35 mg, 0.232 mmol, 2 equip), SPhos (9.7 mg, 0.023 mmol, 0.2 equip), tripotassium phosphate (49.2 mg, 0.232 mmol, 2 equip), and palladium acetate (2.6 mg, 0.012 mmol, 0.1 equip) were added and the resulting mixture was stirred overnight. The reaction mixture was diluted with water and ethyl acetate and the layers were separated. The organic phase was washed with saturated sodium bicarbonate, then water, dried over Na2SO4, filtered and concentrated. The residue was purified by MPLC using a dichloromethane-methanol gradient to yield (E)-6-((4-chlorophenyl)(thiazol-2-yl)methyl)-4-styrylquinolin-2(1H)-one.

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. customthe layers were separated
  3. washThe organic phase was washed with saturated sodium bicarbonate
  4. dry with materialwater, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by MPLC

Sources & evidence

ORD record
ord-2c91cf3d77e74c0f8e10807313132459
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

Loading…