2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → HCID 118324140, compound

HRID 1778310Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[O:13])[CH:10]=2)[N:5]=[C:4]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:3]=1.F[C:27]1[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=1)/[CH:30]=[CH:31]/B(O)O.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]>[C:22]([O:21][C:4]1[CH:3]=[C:2](/[CH:31]=[CH:30]/[C:29]2[CH:35]=[CH:36][CH:37]=[CH:27][CH:28]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[O:13])[CH:10]=2)[N:5]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of (4-bromo-2-(tert-butoxy)quinolin-6-yl)(4-chlorophenyl)methanone (157 mg, 0.375 mmol), (E)-(3-fluorostyryl)boronic acid (105.8 mg, 0.637 mmol), Pd(OAc)2 (8.42 mg, 0.0375 mmol), SPhos (30.79 mg, 0.0375 mmol), and K3PO4.H2O (159 mg, 0.75 mmol) in anhydrous THF (2.5 mL) was stirred at 30° C. overnight. The reaction was diluted with EtOAc and water. The organics were concentrated and purified by silica column chromatography (20% EtOAc/heptanes) to yield (E)-(2-(tert-butoxy)-4-styrylquinolin-6-yl)(4-chlorophenyl)methanone. (ES, m/z) [M-tBu]+ 404, 405, 407

Workup

concentrationThe organics were concentrated
custompurified by silica column chromatography (20% EtOAc/heptanes)

Sources & evidence

ORD record: ord-ceef7cc233dc45e1a1349db0da498a94
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266835B2

Reaction notes

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