Water → HCID 86689810, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 5-bromo-6-methoxypyridin-2-amine (1.72 g, 8.47 mmol) in dimethylacetamide (26 mL) was added 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (2.07 mL, 11.0 mmol), palladium tetrakis(triphenylphoshine) (979 mg, 847 μmol) and tribasic potassium phosphate (3.6 g, 16.9 mmol) in water (7.63 mL, 424 mmol). The mixture was sealed in a microwave vial and heated at 150° C. in a microwave for 15 min. Upon cooling, the mixture was diluted with EtOAc and Et2O, washed with water and brine, concentrated on to silica gel, and chromatographed (10% to 40% EtOAc in hexanes) to give 6-methoxy-5-(prop-1-en-2-yl)pyridin-2-amine contaminated with catalyst-derived impurities (−950 mg). 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.34 (d, J=8.0 Hz, 1H), 6.06 (d, J=8.1 Hz, 1H), 5.19 (m, 1H), 5.09 (m, 1H), 4.29 (br. s, 2H), 3.91 (s, 3H), 2.10 (s, 3H).

Provenance & Evidence