Water → 4'-(3-Oxo-3-(pyridazin-4-yl)-1-o-tolylpropyl)biphenyl-4-carboxylic acid

HRID 1527969Notes

Reaction equation

O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH2:16][C:17]([C:19]2[CH:24]=[CH:23][N:22]=[N:21][CH:20]=2)=[O:18])=[CH:11][CH:10]=1.B([C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=1)(O)O>O1CCOCC1>[O:18]=[C:17]([C:19]1[CH:24]=[CH:23][N:22]=[N:21][CH:20]=1)[CH2:16][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([C:35]2[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=2)=[CH:14][CH:13]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

Water (1 mL) and 2 M aq. sodium carbonate solution (0.39 mL, 0.78 mmol) were added at room temperature to a degassed solution of 3-(4-bromophenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one (100 mg, 262 μmol), 4-boronobenzoic acid (53.8 mg, 315 μmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (11 mg, 13 μmol) in 1,4-dioxane (1.5 mL). After heating at 80° C. for 4 h the reaction mixture was partitioned between ethyl acetate and sat. aq. ammonium chloride solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. After chromatography (SiO2; gradient heptane/ethyl acetate 1:1 to ethyl acetate) the title compound was obtained (33 mg, 30%). Light yellow solid, MS: 423.2 [M+H]+.

Workup

customwas partitioned between ethyl acetate and sat. aq. ammonium chloride solution
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-7ba81409f8894953aa4f2417a8f77bfd
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090565B2

Reaction notes

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