تفاعل #42566

معادلة التفاعل

methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate

thiazole

n-butyl lithium

→

methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate

المردود 99.1%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةThe mixture was then heated at 80° C. for 2 h, at which time it
3. 3
   درجة الحرارةto cool
4. 4
   أخرىpartitioned between ethyl acetate and water
5. 5
   غسيلThe organic layers were washed with brine
6. 6
   تجفيفdried (magnesium sulfate)
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was chromatographed on silica gel

الإجراء التجريبي

To a −78° C. solution of thiazole (1.2 g) in THF (25 mL) was added n-butyl lithium (1.6 M in hexanes, 10 mL). The mixture was stirred for 30 min and then allowed to warm to 0° C. in an ice/water bath. Zinc chloride (1M in ethyl ether, 40 mL) was added and the mixture was stirred for 1 h, at which time methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate (5.1 g) in THF (20 mL) was added, followed by Pd(PPh3)4 (palladium tetrakis triphenylphosphine) (0.68 g). The mixture was then heated at 80° C. for 2 h, at which time it was allowed to cool and partitioned between ethyl acetate and water. The organic layers were washed with brine, dried (magnesium sulfate), and concentrated. The residue was chromatographed on silica gel using ethyl acetate/heptane (50/50) to give 4.5 g of methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate.

المصدر