Sodium Acetate → 5-(4-Fluorophenyl)-7-(4-imidazol-2-ylpiperidyl)thiopheno[3,2-b]pyridine

HRID 378943Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:5]=[C:4]2[CH:15]=[CH:16][S:17][C:3]=12.Cl.[NH:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C([O-])(=O)C.[Na+]>C(O)CO.C(OC(=O)C)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[C:4]3[CH:15]=[CH:16][S:17][C:3]3=[C:2]([N:27]3[CH2:26][CH2:25][CH:24]([C:20]4[NH:21][CH:22]=[CH:23][N:19]=4)[CH2:29][CH2:28]3)[CH:7]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 7-chloro-5-(4-fluorophenyl)thieno[3,2-b]pyridine (146 mg, 0.53 mmol), 4-(1H-imidazol-2-yl)piperidine. hydrochloride (U.S. Pat. No. 4,431,653) (100 mg, 0.53 mmole) and sodium acetate (50 mg) in ethylene glycol (10 mL) is stirred and heated at 160° C. for about 16 hours. It is then cooled, diluted with ethylacetate (15 mL), and washed with water (3×15 mL). The organic layer is dried over sodium sulfate, filtered, and concentrated. The residue is purified by preparative thin layer chromatography to give 5-(4-fluorophenyl)-7-(4-imidazol-2-ylpiperidyl)thiopheno[3,2-b]pyridine (36 mg, 18% yield) as a white solid, m.p. 95° C. (compound 1).

Workup

temperatureIt is then cooled
washwashed with water (3×15 mL)
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue is purified by preparative thin layer chromatography

Sources & evidence

ORD record: ord-72a49192428048808f259b5fc31ce228
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06297256B1

Reaction notes

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