Diethyl Ether → HCID 68182901, compound

Participants

Reaction Steps

In a 250 mL round bottomed flask was placed 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-6,7-dihydro-1,3-benzothiazol-4(5H)-one (505.1 mg, 1.783 mmol) and tetrahydrofuran (50 mL). To the mixture was added a solution of 4-chlorophenylmagnesium bromide in ether (1M, 3.0 mL, 3.0 mmol) and the mixture was stirred for 4 hr at rt. To the mixture were added a saturated aqueous solution of NH4Cl (50 mL) and water (50 mL) and the resulting mixture was extracted with EtOAc (50 mL×2). The combined organic phases were dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain crude 4-(4-chlorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4,5,6,7-tetrahydro-1,3-benzothiazol-4-ol as a yellowish off-white crystalline solid which was used in the next step without further purification.

Provenance & Evidence