2,4-Dichlorobenzenethiol → 7-[(2,4-Dichlorophenyl)thio]thieno[3,2-b]pyridine-6-carbonitrile
Reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[CH:11][S:12][C:3]=12.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[SH:21]>CN(C)C=O>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[S:21][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[CH:11][S:12][C:3]=12Participants
Procedure
A mixture of 7-chlorothieno[3,2-b]pyridine-6-carbonitrile (200 mg, 1.03 mmol) and 2,4-dichlorothiophenol (202.9 mg, 1.13 mmol) in 5 mL of N,N-dimethylformamide is stirred at room temperature for 1 hour, and then concentrated in vacuo. The resulting residue is treated with water and stirred for 1 hour. The precipitate is filtered, washed with water, air dried, and then purified by flash column chromatography eluting with a gradient of 5% ethyl acetate in hexane to 20% ethyl acetate in hexane to provide 249.0 mg of 7-[(2,4-dichlorophenyl)thio]thieno[3,2-b]pyridine-6-carbonitrile as a white solid, mp 126–128° C.; 1H NMR (DMSO-d6) δ 7.47 (dd, J=6,2 Hz, 1H), 7.54 (d, J=6 Hz, 1H), 7.73 (d, J=4 Hz, 1H), 7.88 (d, J=2 Hz, 1 H), 8.43 (d, J=4 Hz, 1H), 9.09 (s, 1H); MS 336.9, 339.0 (M+H)+.
Workup
- concentrationconcentrated in vacuo
- additionThe resulting residue is treated with water
- stirringstirred for 1 hour
- filtrationThe precipitate is filtered
- washwashed with water, air
- customdried
- custompurified by flash column chromatography
- washeluting with a gradient of 5% ethyl acetate in hexane to 20% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-22544021c5054c3287aa710192c5c1e4
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07276519B2
Reaction notes
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