Tetrahydrofuran → N-(5-bromo-4-methylpyridin-3-yl)tetrahydro-2H-pyran-4-carboxamide

HRID 468713

반응식

HRID 468713 반응식
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.O1CCCC1.C[Mg]Br.[O:18]1[CH2:23][CH2:22][CH:21]([C:24](OC)=[O:25])[CH2:20][CH2:19]1>C1(C)C=CC=CC=1.ClCCl>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:8][C:24]([CH:21]2[CH2:22][CH2:23][O:18][CH2:19][CH2:20]2)=[O:25])[CH:5]=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 70606795-Bromo-4-methylpyridin-3-amineHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 67974771N-(5-bromo-4-methylpyridin-3-yl)tetrahydro-2H-pyran-4-carboxamide수율 26%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 5-bromo-4-methylpyridin-3-amine (128.9 mg, 0.6892 mmol) in tetrahydrofuran (4.0 mL, 49 mmol) at 0° C. was added 1.4 M of methylmagnesium bromide in toluene (0.55 mL). After stirring at 0° C. for 10 minutes, methyl tetrahydro-2H-pyran-4-carboxylate (92.00 g, 638.1 mmol) was added. The reaction mixture was stirred overnight while warming to room temperature. The reaction mixture was poured into dichloromethane, washed with saturated aqueous NaHCO3, dried over MgSO4, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (12 g silica, solvent gradient: 0-10% methanol in dichloromethane) to yield 53.5 mg (26%) of N-(5-bromo-4-methylpyridin-3-yl)tetrahydro-2H-pyran-4-carboxamide. LCMS (ESI): M+H=299.2.

후처리

  1. stirringThe reaction mixture was stirred overnight
  2. temperaturewhile warming to room temperature
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe crude product was purified via flash chromatography on silica gel (12 g silica, solvent gradient: 0-10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-0d18ffedee634b008e7068232643a32e
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

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