3-(5-BROMOTHIAZOL-2-YLOXY)PHENOL synthesis

Yield:904961-08-6 64%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 130; for 2 h;

Steps:

1A

EXAMPLE 1; N-(3-{2-[3-(cyclohexylmethoxy)phenoxy]-1,3-thiazol-5-yl}-1-methylprop-2-ynyl)acetamide; EXAMPLE 1A; A solution of 2,5-dibromothiazole (5 g, 20.58 mmol) and resorcinol (4.53 g, 41.16 mmol) in DMF (100 mL) was treated with potassium carbonate (2.86g, 20.58 mmol) and the mixture was heated at 130° C. for 2 h. The reaction was cooled to 25° C., poured into water (400 mL) and extracted with diethyl ether (3×250 mL). The combined organic layers were washed with water (3×150 mL) and brine (150 mL), dried over sodium sulfate and concentrated on a rotary evaporator. The crude concentrate (6.4 g) was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 25% ethyl acetate in hexanes to provide 3.6 g (64%) of Example 1a as awhite solid. ¹H NMR (300 MHz, DMSO-D6) δ ppm 6.67-6.88 (m, 2H) 7.28 (t, J=8.27 Hz, 1H) 7.51 (s, 1H) 9.90 (s, 1H); MS (ESI) m/z 273.6(M+H)⁺.

References:

US2006/178400,2006,A1 Location in patent:Page/Page column 20