Bromide ion → HCID 71153192, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was added 2-(2-(3-bromophenyl)imidazo[1,2-a]pyridin-7-yl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (37 mg, 0.088 mmol), cyclopropylboronic acid (22.74 mg, 0.265 mmol), TRICYCLOHEXYLPHOSPHINE (12.37 mg, 0.044 mmol), Toluene (1 mL), Water (0.3 mL) and potassium phosphate tribasic (74.9 mg, 0.353 mmol). The solution was purged with nitrogen for 5 min and then PALLADIUM(II) ACETATE (1.981 mg, 8.82 μmol) was added. The reaction vial was sealed and heated to 110° C. for 16 hours. The reaction turned black and was checked by LC/MS. The reaction was complete as indicated by no starting bromide being present. The reaction was cooled to rt and extracted with EtOAc 4×. The organic fractions were combined, dried over Na2SO4 and evaporated in vacuo. The crude oil was purified by silica gel chromatography eluting with 5% Acetone/95% Hexanes to 60% Acetone/40% Hexanes. The pure fractions were combined and evaporated in vacuo affording 2-(2-(3-cyclopropylphenyl)imidazo[1,2-a]pyridin-7-yl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (24 mg, 0.058 mmol, 66.1% yield) as an off white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 8.79 (br. s., 1H), 8.29 (d, J=4.5 Hz, 1H), 7.97 (s, 1H), 7.92 (s, 1H), 7.81 (s, 1H), 7.78 (d, J=4.5 Hz, 1H), 7.38 (t, J=4.5 Hz, 1H), 7.10 (d, J=4.5 Hz, 1H), 2.98 (s, 3H), 2.82 (s, 3H), 2.01 (m, 1H), 1.02 (m, 2H), 0.86 (m, 2H), LC/Mass spec. (Method 1) RT=1.89 min. Mass=381.2 (MH)+.

Provenance & Evidence