6-Chloronicotinic acid → 2-(4-Methoxyphenyl)benzo[b]thiophen-3-yl 6-chloropyrid-3-yl ketone

HRID 1386979Notes

Reaction equation

HRID 1386979 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[CH:20]=2)=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([C:20]2[C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[S:23][C:19]=2[C:16]2[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=2)=[O:8])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 792226-Chloronicotinic acidHCID 41373912-(4-Methoxyphenyl)benzothiophene

Product 1

HCID 108097592-(4-Methoxyphenyl)benzo[b]thiophen-3-yl 6-chloropyrid-3-yl ketoneYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By essentially following the procedure detailed in Example 1, Part C, the title compound was prepared from 6-chloronicotinic acid and 2-(4-methoxyphenyl)benzo[b]thiophene (Example 3, Part A) in 31% yield as a yellow solid following flash chromatography (SiO2; CH2Cl2).

Sources & evidence

ORD record
ord-d9bb777a10644bfe92d221b27d71541e
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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