반응 #42566

반응 방정식

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

thiazole

n-butyl lithium

→

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

수율 99.1%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도The mixture was then heated at 80° C. for 2 h, at which time it
3. 3
   온도to cool
4. 4
   기타partitioned between ethyl acetate and water
5. 5
   세척The organic layers were washed with brine
6. 6
   건조dried (magnesium sulfate)
7. 7
   농축concentrated
8. 8
   기타The residue was chromatographed on silica gel

실험 절차

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.

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