1,4-Dioxane → 2-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-6,7-dihydro-5H-quinolin-8-one

HRID 2279265Notes

Reaction equation

HRID 2279265 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:12])[C:4]=2[N:3]=1.C([Sn](CCCC)(CCCC)[C:18]1[S:22][C:21]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[N:20][C:19]=1[CH3:29])CCC.O1CCOCC1>ClCCl.[OH-].[Na+].C([O-])(O)=O.[Na+]>[CH3:29][C:19]1[N:20]=[C:21]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[S:22][C:18]=1[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:12])[C:4]=2[N:3]=1

Participants

7

Reactant 3

HCID 312751,4-DioxaneHCID 146801122-Chloro-5,6,7,8-tetrahydroquinolin-8-oneHCID 90008082Tributyl-[4-methyl-2-(3-pyridyl)thiazol-5-yl]stannane

Product 1

HCID 1180818392-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-6,7-dihydro-5H-quinolin-8-oneYield 92%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

In a MW vial, 2-chloro-6,7-dihydro-5H-quinolin-8-one (0.215 g, 1.18 mmol) and tributyl-[4-methyl-2-(3-pyridyl)thiazol-5-yl]stannane (0.500 g, 1.07 mmol) were stirred in 1,4-dioxane (3.6 mL, 1.07 mmol) at ambient temperature. This yellow solution was degassed with an argon flux for 10 min and Tetrakis(PPh3)Pd(O) (0.124 g, 0.107 mmol) was added. The solution was irradiated in MW at 160° C. for 40 min. The crude was diluted with dichloromethane, NaOH (1 M) and NaHCO3 sat aq were added and aqueous layer was extracted 3 times with dichloromethane. The organic phase was then washed with brine, dried over Na2SO4 anhydrous, filtered and concentrated. Purification by column with a gradient of dichloromethane+0-10% methanol gave the title compound as a beige solid, yield: 92%. LCMS: 0.81 Min, 322 (M+1).

Workup

  1. customThis yellow solution was degassed with an argon flux for 10 min
  2. customThe solution was irradiated in MW at 160° C. for 40 min
  3. additionsat aq were added
  4. extractionaqueous layer was extracted 3 times with dichloromethane
  5. washThe organic phase was then washed with brine
  6. dry with materialdried over Na2SO4 anhydrous
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column with a gradient of dichloromethane+0-10% methanol

Sources & evidence

ORD record
ord-665278a5cf16472caf76f421d09cc3bd
Source dataset
uspto-grants-2015_09
Patent number
US09133218B2

Reaction notes

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