반응 #478461

반응 방정식

2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

5-Bromo-pyridin-3-ylamine

s-PHOS

potassium phosphate

→

solid

수율 43.5%

4-(5-Amino-pyridin-3-yl)-2-chloro-benzonitrile

수율 43.5%

용매

toluene

반응 조건

후처리

1. 1
   기타(General Suzuki reaction procedure 1)
2. 2
   여과After filtration and concentration
3. 3
   workup.DISSOLUTIONthe residue was dissolved into CH2Cl2
4. 4
   workup.ADDITIONmixed with celite
5. 5
   농축After concentration

실험 절차

(General Suzuki reaction procedure 1) A mixture of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.32 g, 5 mmol), 5-Bromo-pyridin-3-ylamine (865 mg, 5 mmol), s-PHOS (103 mg, 0.25 mmol), potassium phosphate (2.12 g, 10 mmol) and Pd2(dba)3 (41.2 mg, 0.1 mmol) in toluene (20 mL) was heated to 95° C. overnight (18 h). After filtration and concentration, the residue was dissolved into CH2Cl2 and mixed with celite. After concentration, the residue was loaded to column (MeOH—CH2Cl2, v/v, 1%-3.5%) and resulted in a light brown solid (500 mg). 1HNMR (400 MHz, CDCl3): δ 4.82 (brs, 2H), 7.11 (t, J=2 Hz, 1H), 7.55 (dd, J=2 Hz, 8 Hz, 1H), 7.69 (d, J=2 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 8.16 (d, J=2 Hz, 1H), 8.22 (d, J=2 Hz, 1H).

출처