Nitrogen → 1-(3-(3-(4-Methylpiperazin-1-yl)quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethanone

HRID 2175160Notes

Reaction equation

HRID 2175160 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[CH:15]4)=[N:9][N:10]=2)[CH:7]=1.N#N.C([Sn](CCCC)(CCCC)[C:36]([O:38]CC)=[CH2:37])CCC>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>[CH3:28][N:25]1[CH2:26][CH2:27][N:22]([C:16]2[CH:17]=[N:18][C:19]3[C:14]([CH:15]=2)=[CH:13][C:12]([S:11][C:8]2[N:6]4[CH:7]=[C:2]([C:36](=[O:38])[CH3:37])[CH:3]=[CH:4][C:5]4=[N:10][N:9]=2)=[CH:21][CH:20]=3)[CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 866962936-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-ylthio)-3-(4-methylpiperazin-1-yl)quinoline

Product 1

HCID 866962941-(3-(3-(4-Methylpiperazin-1-yl)quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethanone

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of (86.1) (80 mg, 0.176 mmol) and PdCl2(PPh3)2 (12.3 mg, 0.018 mmol) in dioxane (6 ml) was bubbled by N2 for 10 min, then tributyl(1-ethoxyvinyl)stannane (127 mg, 0.351 mmol) was added and the solution was heated at 110° C. under N2 for 3 hours in oil bath. The reaction mixture was quenched with KF solution and extracted with EtOAc for three times. The combined extract was washed with brine and dried over anhydrous Na2SO4. Solvent was evaporated and the crude was dissolved in MeOH (10 ml). Drops of 3N HCl solution were added and the solution was then stirred at rt for 4 hours. Solvent was evaporated and the residue was purified on flash chromatography (gradient eluent: MeOH/DCM from 0-10%) to afford the title compound as yellow solid (0.16 g, >100%, contains some impurities). LCMS (method A): [M+H]+=419.2, tR=1.45 min.

Workup

  1. customThe reaction mixture was quenched with KF solution
  2. extractionextracted with EtOAc for three times
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customSolvent was evaporated
  7. dissolutionthe crude was dissolved in MeOH (10 ml)
  8. additionDrops of 3N HCl solution were added
  9. customSolvent was evaporated
  10. customthe residue was purified on flash chromatography (gradient eluent: MeOH/DCM from 0-10%)

Sources & evidence

ORD record
ord-dcbb8c2d605e4bb5859a4c2f30a61f36
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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