Potassium Carbonate → HCID 66690711, compound

Temperature

90 °C

A degassed solution of n-propanol (40 mL) and water (10 mL) was added to a mixture of ethyl 8-bromoimidazo[1,2-a]pyridine-6-carboxylate (1.0 g, 3.72 mmol), (4-methylphenyl)boronic acid (0.66 g, 4.83 mmol), (tetrakistriphenylphosphine) palladium(0) (0.22 g, 0.19 mmol) and potassium carbonate (1.54 g, 11.2 mmol). The mixture was heated to 90° C. After 18 h, sodium hydroxide (3N in water; 3 mL) and methanol (20 mL) was added. The mixture was stirred at 90° C. for another 48 h. The mixture was cooled to ambient temperature and filtered with Celite. The filtrate was concentrated. The water was azeotropically removed with repeated concentration from acetonitrile. The crude mixture was taken up in methanol and small amount of water and loaded onto a 25 g pre-equilibrated SCX column. The column was washed with 5× column volumes of methanol to remove impurities. The column was then washed with 3× column volumes of 2 M ammonia/methanol to elude the titled product (0.90 g): LC-MS [M+1]=253.2.

1. temperatureThe mixture was cooled to ambient temperature
2. filtrationfiltered with Celite
3. concentrationThe filtrate was concentrated
4. customThe water was azeotropically removed
5. concentrationconcentration from acetonitrile
6. washThe column was washed with 5× column volumes of methanol
7. customto remove impurities
8. washThe column was then washed with 3× column volumes of 2 M ammonia/methanol

ORD record

ord-745100c03a1b461a8262f9b1cb78414b

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238647B2