Triethylamine → 3-Bromo-1-(6-bromo-2-methylpyridin-3-yl)pyrrolidin-2-one

HRID 705498

반응식

HRID 705498 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:17][CH:18]([CH2:22][CH2:23]Br)[C:19](Cl)=[O:20].[OH-].[K+]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Br:17][CH:18]1[CH2:22][CH2:23][N:9]([C:5]2[C:6]([CH3:8])=[N:7][C:2]([Br:1])=[CH:3][CH:4]=2)[C:19]1=[O:20]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 44131432,4-Dibromobutyryl chlorideHCID 144180456-Bromo-2-methylpyridin-3-amine

생성물 1

HCID 899059653-Bromo-1-(6-bromo-2-methylpyridin-3-yl)pyrrolidin-2-one

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

A 500 mL round-bottom flask was charged with 6-bromo-2-methylpyridin-3-amine (8.15 g, 43.6 mmol), THF (180 mL) and triethylamine (9.72 mL, 69.7 mmol). The mixture was cooled to 0° C. and 2,4 dibromobutanoyl chloride (6.39 mL, 48.4 mmol) in THF (45 mL) was added dropwise into the reaction mixture over 30 min. A LC/MS analysis indicated the consumption of the starting material in 1 hour at room temperature. To the reaction mixture was added tetrabutylammonium bromide (0.702 g, 2.179 mmol), followed by 20 mL of 5 M aq KOH solution dropwise. The reaction mixture was stirred at room temperature under argon overnight. A LC/MS analysis confirmed the reaction was complete. Ethyl acetate (50 mL) was added to the reaction. The organic layer was separated and washed with water (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated to a dark solid (18.5 g), which was used directly to next step. MS (ESI) 334 (M+H).

후처리

  1. customthe consumption of the starting material in 1 hour at room temperature
  2. customThe organic layer was separated
  3. washwashed with water (50 mL), brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a dark solid (18.5 g), which

출처 및 근거

ORD 기록
ord-42a3fed68d794cf98dcbaccc98cfc39f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174965B2

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