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

HRID 1814495Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[CH3:10])=[O:4].C([Li])CCC.[Br:16][C:17]1[CH:24]=[CH:23][C:20](C#N)=[CH:19][CH:18]=1>O1CCCC1>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([C:1]2[NH:2][C:3](=[O:4])[C:5]3[CH:9]=[CH:8][S:7][C:6]=3[CH:10]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: -70 °C

Procedure

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%). (281-2) 4-(4-Ethylpiperazin-1-yl)-6-(4-bromophenyl)thieno[3,2-c]pyridine

Workup

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

Sources & evidence

ORD record: ord-bf6de1efc3264dbcab6b5435ae72ddc7
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875761B2

Reaction notes

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