تفاعل #172089

معادلة التفاعل

(R)-tert-butyl 1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamate

pyridine-2-boronic acid pinacol ester

Cs2CO3

→

(R)-tert-butyl 1-amino-1-oxo-3-(4-(pyridin-2-yl)phenyl)propan-2-ylcarbamate

المردود 33.5%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىwas degassed with argon
2. 2
   workup.ADDITIONWater and EtOAc were added
3. 3
   أخرىThe organic phase was separated
4. 4
   تجفيفdried over Na2SO4
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue was purified by a silica gel column, which
7. 7
   غسيلwas eluted with 20-100% EtOAc in hexane

الإجراء التجريبي

A mixture of (R)-tert-butyl 1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamate (970 mg, 2.48 mmol), pyridine-2-boronic acid pinacol ester (505 mg, 2.46 mmol), dppf (275 mg, 0.496 mmol), Cs2CO3 (1.00 g, 3.06 mmol), Pd(OAc)2 (56 mg, 0.249 mmol) and CuCl (25 mg, 0.252 mmol) in DMF (10 mL) was degassed with argon, then was stirred at 100 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, which was eluted with 20-100% EtOAc in hexane to give (R)-tert-butyl 1-amino-1-oxo-3-(4-(pyridin-2-yl)phenyl)propan-2-ylcarbamate (281 mg).

المصدر