Styrylboronic acid → HCID 118324017, compound

HRID 1778303Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[OH:13])[CH:10]=2)[N:5]=[C:4]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH:3]=1.[CH:34](/B(O)O)=[CH:35]\[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>C1COCC1.C(Cl)Cl.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:30]([O:29][C:4]1[CH:3]=[C:2](/[CH:34]=[CH:35]/[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[OH:13])[CH:10]=2)[N:5]=1)([CH3:31])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of (4-bromo-2-(tert-butoxy)quinolin-6-yl)(4-chlorophenyl)(4-methoxyphenyl)methanol (107 mg, 0.203 mmol), (E)-styrylboronic acid (60 mg, 0.406 mmol), Pd(OAc)2 (4.56 mg, 0.0203 mmol), SPhos (16.7 mg, 0.0406 mmol) and K3PO4.H2O (86.2 mg, 0.406 mmol) in anhydrous THF (1 mL) was heated at 35° C. overnight. The reaction was diluted with DCM and water. The organics were washed with water and concentrated. The crude material was purified by silica column (40-55% EtOAc/hexanes) to yield (E)-(2-(tert-butoxy)-4-styrylquinolin-6-yl)(4-chlorophenyl)(4-methoxyphenyl)methanol.

Workup

washThe organics were washed with water
concentrationconcentrated
customThe crude material was purified by silica column (40-55% EtOAc/hexanes)

Sources & evidence

ORD record: ord-e62a96e737f24300b1695bfe1f71e749
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266835B2

Reaction notes

Loading…