تفاعل #69893

معادلة التفاعل

Na2CO3

3-Bromopyridine-2-carboxylic acid methyl ester

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

→

3′,6′-dihydro-2′H-[3,4]bipyridinyl-2,1′-dicarboxylic acid 1′-t-butyl ester 2-methyl ester

المردود 64.2%

المذيبات

THF

water

EtOAc

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas maintained
2. 2
   درجة الحرارةat reflux in an oil bath
3. 3
   غسيلwashed with saturated aqueous NaCl (2×100 mL)
4. 4
   تجفيفThe organic layer was dried over anhydrous Na2SO4
5. 5
   تركيزconcentrated under vacuum
6. 6
   غسيلeluted with EtOAc/PE (1:20)

الإجراء التجريبي

3-Bromopyridine-2-carboxylic acid methyl ester (4.0 g, 18.6 mmol, 1.0 eq.) was combined with a solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (5.8 g, 18.6 mmol, 1.0 eq.) in THF (100 mL), under nitrogen. A solution of Na2CO3 (7.9 g, 74.5 mmol, 4.0 eq.) in water (37 mL) was added, followed by the addition of PdCl2(PPh3)2 (650 mg, 930 μmol, 0.05 eq.). The resulting solution was stirred for 14 hours while the temperature was maintained at reflux in an oil bath. The resulting solution was diluted with EtOAc (100 mL), then washed with saturated aqueous NaCl (2×100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:20) to yield 3′,6′-dihydro-2′H-[3,4]bipyridinyl-2,1′-dicarboxylic acid 1′-t-butyl ester 2-methyl ester (3.8 g) as colorless oil.

المصدر