Diisopropylethylamine → Methyl 5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinate

HRID 72436

반응식

HRID 72436 반응식
Cl[C:2]1[N:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1([CH:19]2[CH2:23][CH2:22][CH2:21][NH:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:12][C:9]1[CH:10]=[N:11][C:2]([N:20]2[CH2:21][CH2:22][CH2:23][CH:19]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2618922-PhenylpyrrolidineHCID 2764318Methyl 2,5-Dichloronicotinate

생성물 1

HCID 67958237Methyl 5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinate수율 90.9%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a solution of Methyl 2,5-dichloronicotinate (120 mg, 0.58 mmol,) in isopropanol (10 ml), 2-phenylpyrrolidine (86 mg, 0.58 mmol, available from Matrix Scientific #018619) and N,N-Diisopropylethylamine (90 mg, 0.70 mmol) were added. The mixture was heated under reflux overnight. After cooling to room temperature, the mixture was evaporated and the residue was dissolved in ethyl acetate (10 ml), washed with water (10 ml) and brine (10 ml), dried over Na2SO4 and evaporated in vacuo. The crude residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 20:1 to afford the title compound (D72) (167 mg) as colorless oil.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customthe mixture was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate (10 ml)
  5. washwashed with water (10 ml) and brine (10 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo
  8. customThe crude residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 20:1

출처 및 근거

ORD 기록
ord-5e3375791b904b1f97f0e2e9f6e535f8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828987B2

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