Tetrahydrofuran → Ethyl 2-(2-acetamidopyridin-4-yl)-4-(naphthalen-2-ylmethyl)thiazole-5-carboxylate

To a mixture of ethyl 2-(2-acetamidopyridin-4-yl)-4-bromothiazole-5-carboxylate (190 mg, 0.510 mmol) and bis(tri-t-butylphosphine)palladium(0) (65.6 mg, 0.128 mmol) under nitrogen was added a 0.500 M solution of 2-napthylmethylzinc bromide in THF (3.60 mL, 1.80 mmol). The reaction was stirred at room temperature for 5 minutes, then at 60 degrees for 1 hour. Another portion of bis(tri-t-butylphosphine)palladium(0) (60.0 mg, 0.117 mmol) was added, followed by another portion of 0.500 M solution of 2-napthylmethylzinc bromide in THF (3.00 mL, 1.50 mmol), and the reaction was heated at 60 degrees for an additional 45 minutes. The reaction was cooled to room temperature and quenched with saturated ammonium chloride (10 mL). The mixture was extracted with ethyl acetate (2×20 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/hexane=0/100→100/0) to give 100 mg of the title compound. (40% yield). LC/MS (FA) ES+ 432.

1. waitat 60 degrees for 1 hour
2. temperaturethe reaction was heated at 60 degrees for an additional 45 minutes
3. temperatureThe reaction was cooled to room temperature
4. customquenched with saturated ammonium chloride (10 mL)
5. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
6. dry with materialthe combined organic layers were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane=0/100→100/0)

ORD record

ord-96c856dddf0248b09eb0f42e1b736aec

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796271B2