Imidazole → 2-(4-fluorophenyl)-7-(1H-imidazol-1-yl)-3-pyridin-4-ylpyrazolo[1,5-a]pyridine

HRID 1373836Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>CS(C)=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:9]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([N:24]4[CH:28]=[CH:27][N:26]=[CH:25]4)[N:7]3[N:8]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 7-chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridine (100 mg) and imidazole (5 eq.) in dimethylsulfoxide (2 mL) in sealed tube was heated at 120° C. overnight. The mixture was evaporated to dryness and purified by preparative thin layer chromatography to give 2-(4-fluorophenyl)-7-(1H-imidazol-1-yl)-3-pyridin-4-ylpyrazolo[1,5-α]pyridine. 1H NMR (CDCl3): δ 8.65 (d, 2H, J=5,6 Hz), 7.96 (s, 1H), 7.60 (d, 1H, J=9.5 Hz), 7.44–7.47 (m, 2H), 7.34–7.38 (m, 4H), 7.28 (d, 2H, J=5.7 Hz), 7.02 (m, 2H); MS m/z 356 (M+1).

Workup

customThe mixture was evaporated to dryness
custompurified by preparative thin layer chromatography

Sources & evidence

ORD record: ord-c3fb5adecf2a4bcea31be6900fa8697c
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163940B2

Reaction notes

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