Sodium Carbonate → 3-[3-(2-Cyanothien-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxylic acid methyl ester

温度

80 °C

3-Bromoimidazo[1,2-α]pyridine-7-carboxylic acid methyl ester (0.63 g, 2.47 mmol) and 3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]thiophene-2-carbonitrile (0.55 g, 1.76 mmol) were suspended in 1,2-dimethoxyethane (10 ml) and 2N sodium carbonate solution (5 ml) and degassed with nitrogen for 30 min before addition of tetrakis(triphenylphosphine)palladium(0) (0.14 g, 0.12 mmol). The mixture was heated at 80° C. for 18 h then cooled to room temperature. The mixture was partitioned between ethyl acetate (100 ml) and water (50 ml). The organic layer was washed with brine, dried over sodium sulfate and pre-adsorbed onto silica gel. Purification by silica gel chromatography eluting with dichloromethane/methanol/conc. ammonia (gradient 99:1:0.1 through to 97:2:0.2) gave the title compound (0.59 g, 94%) as pale brown needles. 1H NMR (400 MHz, CDCl3) δH 3.98 (3H, s), 7.35 (1H, d, J 5), 7.48 (1H, dd, J 7 and 2), 7.65-7.75 (3H, m), 7.93 (2H, m), 8.43 (1H, s), 8.54 (1H, dd, J 7 and 1); m/z (ES+) 360 (M++H).

1. temperaturethen cooled to room temperature
2. customThe mixture was partitioned between ethyl acetate (100 ml) and water (50 ml)
3. washThe organic layer was washed with brine
4. dry with materialdried over sodium sulfate and pre-adsorbed onto silica gel
5. customPurification by silica gel chromatography
6. washeluting with dichloromethane/methanol/conc

ORDレコード

ord-53c3a5e244e542cb83555ce1314396f7

出典データセット

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06872731B2