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

HRID 41615

反応式

HRID 41615 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0bb624386e104853ab58d588e672c98c
出典データセット
uspto-grants-2013_09
特許番号
US08530663B2

関連ノート

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