Phosphorus oxychloride → Ethyl 4-chloro-3-cyanopyrrolo[1,2-b]pyridazine-6-carboxylate

HRID 1408904노트

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HRID 1408904 반응식
[C:1]([C:3]1[CH:8]=[N:7][N:6]2[CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=[C:5]2[C:4]=1O)#[N:2].O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:4]1[C:5]2[N:6]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=2)[N:7]=[CH:8][C:3]=1[C:1]#[N:2]

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178468548HCID 178468548, 화합물

생성물 1

HCID 69326995Ethyl 4-chloro-3-cyanopyrrolo[1,2-b]pyridazine-6-carboxylate수율 48%

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온도
75 °C

실험 절차

To a round bottom flask was added POCl3 (200 mL) and ethyl 3-cyano-4-hydroxypyrrolo[1,2-b]pyridazine-6-carboxylate (20 g, 80 mmol). The reaction was heated under nitrogen at 75° C. for 2 hours. The reaction was cooled to room temperature and POCl3 was removed under vacuum. The residue was poured onto ice-water. The aqueous solution was extracted with CH2Cl2. The organic layer was washed with saturated sodium carbonate solution, dried and concentrated. The resulting residue was purified by flash silica gel column chromatography to yield 10 g (48%) of the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm: 8.33 (1H, d, J=1.3 Hz), 8.11 (1H, s), 7.41 (1H, d, J=1.6 Hz), 4.41 (2H, q, J=6.8 Hz), 1.41 (3H, t, J=6.8 Hz).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. customPOCl3 was removed under vacuum
  3. additionThe residue was poured onto ice-water
  4. extractionThe aqueous solution was extracted with CH2Cl2
  5. washThe organic layer was washed with saturated sodium carbonate solution
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash silica gel column chromatography

출처 및 근거

ORD 기록
ord-cc339d5f32ca41a5b144890d2d013296
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921368B2

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