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

HRID 1498789Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-f01f87dd0e4d4c619b3cbfda8f6bba81
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09200001B2

Reaction notes

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