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

HRID 877660ノート

反応式

HRID 877660 の反応式
[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]

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178468548HCID 178468548、化合物

生成物 1

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

反応条件

温度
75 °C

実験手順

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. H1 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).

後処理

  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

出典と根拠

ORDレコード
ord-180cb910c93b44ca81223c83f44f51a6
出典データセット
uspto-grants-2015_03
特許番号
US08987268B2

反応ノート

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