Tributylvinyltin → 3-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-vinylpyridazine

HRID 1498789

반응식

HRID 1498789 반응식
Cl[C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH3:13])=[N:11][C:10]([CH3:14])=[N:9]2)[N:5]=[N:6][CH:7]=1.[CH2:15]([Sn](CCCC)(CCCC)C=C)[CH2:16]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:10]1[N:11]=[C:12]([CH3:13])[N:8]([C:4]2[N:5]=[N:6][CH:7]=[C:2]([CH:15]=[CH2:16])[CH:3]=2)[N:9]=1

참가 물질

5

반응물 2

HCID 81998TributylvinyltinHCID 867320485-chloro-3-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazine

생성물 1

HCID 867320493-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-vinylpyridazine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

To a solution of 5-chloro-3-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazine (23-2, 730 mg, 3.48 mmol, 1.0 eq.) in toluene (24 mL) were added tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.17 mmol, 0.05 eq.) and tributyl(vinyl)tin (1.30 mL, 4.52 mmol, 1.3 eq.). The mixture was heated at 120° C. for 3 hours. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel column chromatography (30% ethyl acetate in hexanes) to afford 3-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-vinylpyridazine (23-3) as a white solid. 1H NMR (300 MHz, CDCl3) δ 9.15 (d, 1H, J=1.8 Hz), 8.02 (d, 1H, J=1.8 Hz), 6.73 (dd, 1H, J=17.7, 10.8 Hz), 6.23 (d, 1H, J=17.7 Hz), 5.78 (d, 1H, J=10.8 Hz), 2.95 (s, 3H), 2.44 (s, 3H).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-f01f87dd0e4d4c619b3cbfda8f6bba81
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200001B2

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