Styrylboronic acid → (Z)-(4-chlorophenyl)(4-styrylquinolin-6-yl)(thiazol-4-yl)methanol

HRID 1778309Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[CH:20][CH:19]=[C:18]3Cl)([C:10]2[N:11]=[CH:12][S:13][CH:14]=2)[OH:9])=[CH:4][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.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>C1COCC1.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[CH:20][CH:19]=[C:18]3/[CH:26]=[CH:27]\[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:10]2[N:11]=[CH:12][S:13][CH:14]=2)[OH:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of (4-chlorophenyl)(4-chloroquinolin-6-yl)(thiazol-4-yl)methanol (65 mg, 0.168 mmol), (E)-styrylboronic acid (39.74 mg, 0.269 mmol), Pd(OAc)2 (3.77 mg, 0.0168 mmol), SPhos (13.8 mg, 0.0336 mmol), and K3PO4.H2O (71.25 mg, 0.336 mmol) in anhydrous THF (1.5 mL) was stirred at 30° C. overnight. The reaction was diluted with EtOAc and water. The organics were concentrated and purified by REDSEP GOLD silica column (40% EtOAc/heptanes) to yield (Z)-(4-chlorophenyl)(4-styrylquinolin-6-yl)(thiazol-4-yl)methanol

Workup

concentrationThe organics were concentrated
custompurified by REDSEP GOLD silica column (40% EtOAc/heptanes)

Sources & evidence

ORD record: ord-760cbe80442749c09cd93fe22c182fee
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266835B2

Reaction notes

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