Potassium Carbonate → HCID 58579970, compound

HRID 389259Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=1)[CH3:2].Cl[C:25]1[C:30]([C:31]#[N:32])=[CH:29][CH:28]=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([C:25]2[C:30]([C:31]#[N:32])=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

[4-Methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (0.672 g, 2.1 mmol), 2-chloro-3-pyridinecarbonitrile (0.274 g, 2.0 mmol), and potassium carbonate (0.966 g, 7.0 mmol) were combined in deoxygenated 2:1 DME:H2O (21 mL). Tetrakis(triphenylphosphine)palladium(0) (0.115, 0.1 mmol) was added, and the reaction was stirred at 70° C. for 1 hour. Once no starting material was seen by analytical LCMS and tlc, the mixture was worked-up and purified by silica gel chromatography to give the title compound.

Workup

customin deoxygenated 2:1 DME
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-a14d50035cd64e11bda2fe5dcf18b4e0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378107B2

Reaction notes

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