Triethylamine → 1-[5-Chloro-2-methoxy-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone

HRID 510924Notes

Reaction equation

[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][BH:4][O:3]1.[Cl:10][C:11]1[C:12]([CH3:23])=[C:13](I)[C:14]([O:20][CH3:21])=[C:15]([C:17](=[O:19])[CH3:18])[CH:16]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(N(CC)CC)C>O1CCOCC1.CC#N.CC#N.Cl[Pd]Cl>[Cl:10][C:11]1[C:12]([CH3:23])=[C:13]([B:4]2[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:9])([CH3:1])[O:3]2)[C:14]([O:20][CH3:21])=[C:15]([C:17](=[O:19])[CH3:18])[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (2.2 mL, 15 mmol) was added to a mixture of 1-(5-chloro-3-iodo-2-methoxy-4-methylphenyl)ethanone (2.0 g, 6.2 mmol, from Example 60, Step 2), bis(acetonitrile)palladium(II) chloride (32 mg, 0.12 mmol), 2-(dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl (0.20 g, 0.49 mmol) and triethylamine (2.6 mL, 18 mmol) in 1,4-dioxane (3.7 mL) under N2 and then the mixture was degassed with N2. The reaction was then heated at 100° C. for 3 hours. The mixture was cooled to room temperature, filtered and purified on silica gel column (eluting with 0 to 20% EtOAc in hexanes) to give the desired product (1.3 g, 65%). LCMS calculated for C16H23BClO4 (M+H)+: m/z=325.1. found: 325.1.

Workup

customthe mixture was degassed with N2
temperatureThe mixture was cooled to room temperature
filtrationfiltered
custompurified on silica gel column (eluting with 0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-6adc0ca283334a6a8a24f94c79da469d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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