Benzonitrile, 4-bromo- → 6-(4-bromophenyl)-5H-thieno[3,2-c]pyridin-4-one

To a solution of N-methyl-2-methylthiophene-3-carboxamide (13.0 g) in tetrahydrofuran (130 ml) was dropwise added 2.5 M butyl lithium (74 ml) at −70° C. The reaction solution was stirred at −70° C. for 2 hr, followed by the addition of 4-bromobenzonitrile (15.3 g) at once. After the dry ice/acetone bath was removed, the reaction mixture was back to room temperature. Three hours later, an aqueous solution of saturated ammonium chloride and ether were added thereto, and then the resulting mixture was further stirred for 1 hr. The resulting white precipitates were collected by filtration, and washed with water, ether and n-hexane in this order. The resulting product was dried to give the title compound (4.9 g, yield; 19%).

1. customat −70° C
2. customAfter the dry ice/acetone bath was removed
3. customwas back to room temperature
4. additionThree hours later, an aqueous solution of saturated ammonium chloride and ether were added
5. stirringthe resulting mixture was further stirred for 1 hr
6. customThe resulting white precipitates
7. filtrationwere collected by filtration
8. washwashed with water, ether and n-hexane in this order
9. customThe resulting product was dried

ORD record

ord-ed256ce669d5475ebb1ba775bbd2f691

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06790844B2