Water → Benzyl 2-methoxy-3',6'-dihydro-3,4'-bipyridine-1'(2'H)-carboxylate

HRID 1664805ノート

反応式

HRID 1664805 の反応式
C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)S(O[C:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:17][CH:18]=1)(=O)=O.[CH3:31][O:32][C:33]1[C:38](B(O)O)=[CH:37][CH:36]=[CH:35][N:34]=1.O>CN(C)C=O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:31][O:32][C:33]1[C:38]([C:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:17][CH:18]=2)=[CH:37][CH:36]=[CH:35][N:34]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 11303044benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate

生成物 1

HCID 67439388Benzyl 2-methoxy-3',6'-dihydro-3,4'-bipyridine-1'(2'H)-carboxylate収率 72.8%

試薬・触媒・溶媒 2

HCID 53485975CID 53485975触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Sodium carbonate (2.0 M in water; 4.0 mL, 8.09 mmol) was added to a solution of benzyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (1.26 g, 3.45 mmol) and (2-methoxypyridin-3-yl)boronic acid (0.58 g, 3.79 mmol) in N,N-dimethylformamide (12 mL). Dichloro [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.25 g, 0.345 mmol) was added and the mixture was heated to 70° C. After 2 h, the mixture was cooled to ambient temperature and water was added. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over magnesium sulfate and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) to give the title compound (0.815 g). MS 325.2 (M+1).

後処理

  1. temperaturethe mixture was cooled to ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-8fef8faa2e7b4d648dd17cd31fa09e64
出典データセット
uspto-grants-2011_10
特許番号
US08039460B2

反応ノート

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