Stannane, tributyl(1-ethoxyethenyl)- → 1-(3-(Difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

HRID 1892386Notes

Reaction equation

HRID 1892386 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:23])([F:22])[C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)=[N:9][N:10]=2)[N:7]=1.C([Sn](CCCC)(CCCC)[C:29]([O:31]CC)=[CH2:30])CCC.N1C2C(=CC(CC3N4N=C(C(=O)C)C=CC4=NN=3)=CC=2)C=CC=1>O1CCOCC1.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>[F:22][C:11]([F:23])([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][CH:16]=[CH:15]2)[C:8]1[N:6]2[N:7]=[C:2]([C:29](=[O:31])[CH3:30])[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Participants

6

Reactant 3

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 576910336-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)difluoromethyl)quinoline2×HCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 581904681-(3-(Difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanoneYield 35.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound as a light yellow oil (180 mg, 30%, 80% purity) was synthesized from 6-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)difluoromethyl)quinoline (intermediate R) (500 mg, 1.507 mmol), tributyl(1-ethoxyvinyl)stannane (2.55 mL, 7.54 mmol) and PdCl2(PPh3)2 (106 mg, 0.151 mmol) in 1,4-dioxane using the similar procedure as described in the synthesis of compound 41.2. 1H-NMR (400 MHz, MeOH-d4) δ ppm 9.17 (s, 1H), 8.91 (d, 1H), 8.65 (s, 1H), 8.43 (d, 1H), 8.28 (q, 2H), 7.96 (d, 1H), 7.92 (m, 1H), 2.61 (s, 3H). LCMS (method B): [MH]+=340.1, tR=2.16 min.

Sources & evidence

ORD record
ord-5872339fe35349258e3159caf1caa68a
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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