Potassium Phosphate, Tribasic → (E)-2-((4-chlorophenyl)(4-styrylquinolin-6-yl)methyl)thiazole

HRID 1778290Notes

Reaction equation

HRID 1778290 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)[N:5]=[CH:4][CH:3]=1.[CH:25](/B(O)O)=[CH:26]\[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH:12]([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]=[CH:4][CH:3]=[C:2]3/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 5702628Styrylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 1183239902-((4-Bromoquinolin-6-yl)(4-chlorophenyl)methyl)thiazole

Product 1

HCID 118324044(E)-2-((4-chlorophenyl)(4-styrylquinolin-6-yl)methyl)thiazole

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-((4-bromoquinolin-6-yl)(4-chlorophenyl)methyl)thiazole (28 mg, 0.0674 mmol), (E)-styrylboronic acid (19.9 mg, 0.135 mmol), Pd(OAc)2 (1.5 mg, 0.00674 mmol), SPhos (5.5 mg, 0.022 mmol) and K3PO4 (28.6 mg, 0.135 mmol) was stirred at room temperature overnight under argon. The reaction was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc twice. The organic layers combined were concentrated and the crude material was purified by silica column chromatography (25% EtOAc/hexanes) to yield (E)-2-((4-chlorophenyl)(4-styrylquinolin-6-yl)methyl)thiazole.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc twice
  2. concentrationThe organic layers combined were concentrated
  3. customthe crude material was purified by silica column chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-263bd2f4cf234c66a37c27f058ebe4b6
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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