4-Fluorophenol → 2-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole

HRID 1043655Notes

Reaction equation

Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[CH:9][N:4]2[N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1>ClCCl>[F:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:2]2[S:6][C:5]3=[N:7][CH:8]=[CH:9][N:4]3[N:3]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (1.0 g, 4.90 mmol) and 4-fluorophenol (2.2 g, 19.60 mmol) was heated under microwave irradiation at 135° C. for 3.5 hours. On cooling, the mixture was diluted with dichloromethane (7 mL), adsorbed in silica and purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8) to give 2-(4-fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole as a white solid (610 mg, 53% yield).

Workup

temperatureOn cooling
custompurified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8)

Sources & evidence

ORD record: ord-0cd89577a83c46468ccde53d20b1a5b6
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563550B2

Reaction notes

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