2-Bromopyridine → Methyl 3-(4-fluorophenyl)-2-oxo-2H-1,2'-bipyridine-5-carboxylate

HRID 1909152ノート

反応式

HRID 1909152 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=[O:14])[NH:12][CH:11]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.CN[C@H]1[C@H](NC)CCCC1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13](=[O:14])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH:11]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[CH:9]=2)=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 67339481Methyl 5-(4-fluorophenyl)-6-hydroxynicotinate

生成物 1

HCID 67337652Methyl 3-(4-fluorophenyl)-2-oxo-2H-1,2'-bipyridine-5-carboxylate収率 93.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

To a solution of methyl 5-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate (77.0 mg, 0.31 mmol) in dioxane (2.1 mL) were added 2-bromopyridine (0.15 g, 0.92 mmol), trans-(1R,2R)—N,N′-bismethyl-1,2-cyclohexanediamine (17.7 mg, 0.13 mmol) and potassium carbonate (86.0 mg, 0.62 mmol). The mixture was heated in the microwave reactor at 120° C. for 1 h then heated in an oil bath at 80° C. for 8 h. The mixture was cooled to ambient temperature and dichloromethane was added. The mixture was washed with water, sat. NaHCO3, brine and dried with sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→75% dichloromethane/ethyl acetate) gave the title compound (94 mg). MS 325.1 (M+1).

後処理

  1. temperaturethen heated in an oil bath at 80° C. for 8 h
  2. temperatureThe mixture was cooled to ambient temperature
  3. washThe mixture was washed with water, sat. NaHCO3, brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% dichloromethane→75% dichloromethane/ethyl acetate)

出典と根拠

ORDレコード
ord-8ac49302db134ae4a353644298f28edb
出典データセット
uspto-grants-2013_12
特許番号
US08598209B2

反応ノート

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