Sodium hydride → HCID 86632299, 화합물

HRID 1929530노트

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HRID 1929530 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 86632299HCID 86632299, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-4676f021764847a682c5cf1f61d86b89
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188084B2

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