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Water → 3,6-Dichloro-4-pyrrolidin-1-ylpyridazine

HRID 380325
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HRID 380325 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:7]1[CH:12]=[C:11]([Cl:13])[N:10]=[N:9][C:8]=1[Cl:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:14][C:8]1[N:9]=[N:10][C:11]([Cl:13])=[CH:12][C:7]=1[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 220306484-Bromo-3,6-dichloropyridazine

생성물 1

HCID 124492983,6-Dichloro-4-pyrrolidin-1-ylpyridazine수율 92%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Pyrrolidine (3.36 ml, 40 mmol) was added to a stirred solution/suspension of 4-bromo-3,6-dichloropyridazine (8.3 g, 36 mmol) and potassium carbonate (13.8 g, 0.1 mol) in dry DMF (100 ml) at room temperature under nitrogen. The mixture was stirred at room temperature for 16 hours, then at 60° C. for 3 hours. The reaction was poured into water (250 ml). The aqueous was extracted with ethyl acetate (×3). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with 0.5% methanol/dichloromethane to afford the title pyridazine (7.2 g, 92%) as a colourless oil. 1H NMR (250 MHz , CDCl3) 2.00-2.05 (4H, m), 3.61-3.69 (4H, m), 6.46 (1H, s). MS (ES+) 218 [MH]+, 220 [MH]+.

후처리

  1. waitat 60° C. for 3 hours
  2. extractionThe aqueous was extracted with ethyl acetate (×3)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with 0.5% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-65f19b008697446fab80c4534f0450ef
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06303605B1

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