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

HRID 1498789

反応式

HRID 1498789 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f01f87dd0e4d4c619b3cbfda8f6bba81
出典データセット
uspto-grants-2015_12
特許番号
US09200001B2

関連ノート

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