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

HRID 1909152노트

반응식

HRID 1909152 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8ac49302db134ae4a353644298f28edb
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598209B2

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