Sodium hydride → HCID 86632299、化合物

HRID 1929530ノート

反応式

HRID 1929530 の反応式
[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)[C:9]#[N:10])#[N:2].[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][C:19]=1[CH:20]([CH3:22])[CH3:21].[H-].[Na+]>C1COCC1>[Cl:13][C:14]1[N:15]=[N:16][C:17]([CH:3]([C:1]#[N:2])[C:4]2[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=2)[C:9]#[N:10])=[CH:18][C:19]=1[CH:20]([CH3:22])[CH3:21]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27739363-Cyano-4-fluorobenzylcyanideHCID 140241623,6-Dichloro-4-isopropylpyridazine

生成物 1

HCID 86632299HCID 86632299、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To an ice-cold solution of 5-(cyanomethyl)-2-fluorobenzonitrile (1 eq) and 3,6-dichloro-4-isopropylpyridazine (1.3 eq) (Reference: Org. Prep.+Proc. Int. 1988, 20, 117 and U.S. Pat. No. 4,628,088, 1986) in THF (38 mL, 0.1 M) was added portionwise NaH (1 eq). The reaction was stirred at 0° C. for 15 min and then warmed to RT and stirred for 2 hrs. The reaction was quenched with a sat. aq. NaHCO3 and extracted with EtOAc. The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude was purified by silica gel chromatography, eluting with petroleum ether:EtOAc (8:2) to afford the title compound. 1H NMR (400 MHz, CDCl3) δ: 7.80-7.79 (2H, m), 7.49 (1H, s), 7.31-7.29 (1H, m), 5.63 (1H, s), 3.34-3.28 (1H, m), 1.36-1.29 (6H, m). MS (ES) C16H12ClFN4 required: 314/316. found: 315/317 (M+H)+.

後処理

  1. temperaturewarmed to RT
  2. stirringstirred for 2 hrs
  3. customThe reaction was quenched with a sat. aq. NaHCO3
  4. extractionextracted with EtOAc
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude was purified by silica gel chromatography
  9. washeluting with petroleum ether:EtOAc (8:2)

出典と根拠

ORDレコード
ord-4676f021764847a682c5cf1f61d86b89
出典データセット
uspto-grants-2012_05
特許番号
US08188084B2

反応ノート

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