3-Bromo-3-buten-1-ol → γ-Methylene-6-quinolinepropanol

HRID 500229Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)O1.Br[C:21](=[CH2:25])[CH2:22][CH2:23][OH:24].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:15]1[C:16]2[C:11](=[CH:10][C:9]([C:21](=[CH2:25])[CH2:22][CH2:23][OH:24])=[CH:18][CH:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Palladium acetate (100 mg, 0.6 mmol) was added to a solution of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (8.0 g, 31 mmol) and 3-bromo-3-buten-1-ol (6.2 g, 41 mmol) in toluene (118 mL) and water (12 mL) followed by addition of 2-(dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl (500 mg, 1 mmol). The mixture was stirred at 100° C. for 6 h. After cooling to RT, the mixture was diluted with EtOAc, washed with water and brine. The organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel with EtOAc in methylene chloride (0-50%) to afford the desired product.

Workup

temperatureAfter cooling to RT
washwashed with water and brine
dry with materialThe organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel with EtOAc in methylene chloride (0-50%)

Sources & evidence

ORD record: ord-7486e9eaafc648298087d6777ab08a3a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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