تفاعل #48841

معادلة التفاعل

Potassium carbonate

3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methyl-1,3-thiazol-2-yl)benzamide

1-(3,4-difluorobenzoyl)azetidine

→

desired compound

المردود 11.9%

3-[4-(Azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methyl-1,3-thiazol-2-yl)benzamide

المردود 11.9%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىto reach ambient temperature
2. 2
   أخرىThe residual oil was partitioned between ethyl acetate (50 mL) and water (50 mL)
3. 3
   أخرىThe ethyl acetate layer was separated
4. 4
   غسيلwashed with brine
5. 5
   تجفيفdried (MgSO4)
6. 6
   أخرىevaporated to a residue which
7. 7
   أخرىwas chromatographed on silica
8. 8
   غسيلeluting with a gradient of 0-10% methanol in ethyl acetate

الإجراء التجريبي

Potassium carbonate (143 mg, 1.04 mmol) was added to a mixture of 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methyl-1,3-thiazol-2-yl)benzamide (160 mg, 0.52 mmol) and 1-(3,4-difluorobenzoyl)azetidine (102 mg, 0.52 mmol) in acetonitrile (5.0 mL), and the stirred mixture heated at 160° C. in a ‘Smith Creator Microwave’ for 15 hours. The mixture was allowed to reach ambient temperature and pressure and reduced in vacuo. The residual oil was partitioned between ethyl acetate (50 mL) and water (50 mL). The ethyl acetate layer was separated, washed with brine, dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 0-10% methanol in ethyl acetate, to give the desired compound (30 mg)

المصدر