Hydrochloric Acid → 1-{6-[2-(3-Chloro-2,6-difluoro-phenyl)-imidazol-1-ylmethyl]-5-methoxy-pyridazin-3-yl}-ethanone

HRID 1244251Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([Cl:21])[C:15]=2[F:22])=[C:4]([O:23][CH3:24])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:30]([O:32]CC)=[CH2:31])CCC.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:21][C:16]1[C:15]([F:22])=[C:14]([C:10]2[N:9]([CH2:8][C:5]3[N:6]=[N:7][C:2]([C:30](=[O:32])[CH3:31])=[CH:3][C:4]=3[O:23][CH3:24])[CH:13]=[CH:12][N:11]=2)[C:19]([F:20])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To the mixture of 6-chloro-3-[2-(3-chloro-2,6-difluoro-phenyl)-imidazol-1-ylmethyl]-4-methoxy-pyridazine (95 mg, 0.256 mmol) and tributyl-(1-ethoxy-vinyl)-stannane (139 mg, 1.5 eq.) in toluene (5 mL)is added PdCl2(PPh3)2 (10 mg, 0.05 eq.). The mixture is heated at 110° C. in a sealed tube for 24 hours. On cooling, water (2 mL) and con. HCl (2 mL) are added and the mixture is stirred at room temperature for 2 hours. The mixture is neutralized with aqueous NaOH and extracted with DCM. The combined organic layers are dried and solvent removed. The crude product is purified by PTLC (5% methanol in DCM) to give the title compound (20 mg): LC-MS (M+1) 379.1 (retention time: 0.99 minutes).

Workup

temperatureOn cooling
extractionextracted with DCM
customThe combined organic layers are dried
customsolvent removed
customThe crude product is purified by PTLC (5% methanol in DCM)

Sources & evidence

ORD record: ord-84a421aa7d254c2c870988f8f490d9df
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122546B2

Reaction notes

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