반응 #67779

반응 방정식

4-Iodo-2-methylaniline

3-fluoropyridine-4-carboxylic acid

LiHMDS

→

desired product

수율 59.0%

3-[(4-Iodo-2-methylphenyl)amino]isonicotinic acid

수율 59.0%

용매

THF

반응 조건

후처리

1. 1
   온도to warm to ambient temperature
2. 2
   기타After 36 h the reaction was quenched
3. 3
   workup.ADDITIONby adding solid NH4Cl
4. 4
   여과After filtration the volatiles
5. 5
   기타were removed in vacuo
6. 6
   기타the crude material was purified by flash chromatography

실험 절차

4-Iodo-2-methylaniline (233 mg, 1.00 mmol) and 3-fluoropyridine-4-carboxylic acid (141 mg, 1.00 mmol) were dissolved in dry THF (6.0 ml) under argon and the mixture was cooled to −78° C. A solution of LiHMDS (1.0M in THF, 3.5 ml) was added and the reaction mixture was allowed to warm to ambient temperature. After 36 h the reaction was quenched by adding solid NH4Cl. After filtration the volatiles were removed in vacuo and the crude material was purified by flash chromatography using silica gel and a gradient of 0-10% methanol in DCM as eluent to give 208 mg (588 μmol; 59% yield) of pure desired product.

출처