Sodium Carbonate → 3',6'-dihydro-2'H-[3,4]bipyridinyl-2,1'-dicarboxylic acid 1'-t-butyl ester 2-methyl ester

HRID 41615

반응식

HRID 41615 반응식
[CH3:1][O:2][C:3]([C:5]1[C:10](Br)=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:10]([C:22]2[CH2:23][CH2:24][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:20][CH:21]=2)=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 12828946Methyl 3-bromo-2-pyridinecarboxylate

생성물 1

HCID 582961033',6'-dihydro-2'H-[3,4]bipyridinyl-2,1'-dicarboxylic acid 1'-t-butyl ester 2-methyl ester수율 64.2%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  1. temperaturewas maintained
  2. temperatureat reflux in an oil bath
  3. washwashed with saturated aqueous NaCl (2×100 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under vacuum
  6. washeluted with EtOAc/PE (1:20)

출처 및 근거

ORD 기록
ord-0bb624386e104853ab58d588e672c98c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530663B2

연결된 노트

불러오는 중…