반응 #7168

반응 방정식

phenylboronic acid

cesium carbonate

water

Intermediate 4

4-[2-(tert-butoxycarbonylamino)ethoxy]-N-(3-iodophenyl)-3-methoxyphenylacetamide

→

4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-N-(3-phenylphenyl)phenylacetamide

수율 77.3%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the mixture is heated
2. 2
   온도under reflux for 18 hours under argon atmosphere
3. 3
   기타The solvent is evaporated under reduced pressure
4. 4
   기타the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

실험 절차

Intermediate 4 (500 mg) is dissolved in tetrahydrofuran (10 ml), and thereto are added tetrakis(triphenylphosphine)palladium (0) (110 mg), phenylboronic acid (230 mg), cesium carbonate (1.2 g) and water (2 ml), and the mixture is heated under reflux for 18 hours under argon atmosphere. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-N-(3-phenylphenyl)phenylacetamide (350 mg). This product is treated with 10% hydrogen chloride-methanol to give the desired compound (210 mg).

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