Potassium Carbonate → HCID 68829901, compound

HRID 1986461Notes

Reaction equation

HRID 1986461 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:16]=3)[N:11]=[C:10]([CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:9]=2[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:4][CH:3]=1.[B].[C:41]([O-])(=O)[CH3:42].[K+].Cl[C:47]1[S:48][CH:49]=[CH:50][N:51]=1.[C:52](=[O:55])([O-])[O-:53].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.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.O.C1(C)C=CC=CC=1.C(O)C.CS(C)=O>[C:35]([O:34][C:33]([NH:32][CH2:31][C:9]1[C:10]([CH2:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[N:11][C:12]2[C:17]([C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)=[CH:16][C:15]([C:47]1[S:48][CH:49]=[C:50]([C:52]([O:53][CH2:41][CH3:42])=[O:55])[N:51]=1)=[CH:14][CH:13]=2)=[O:39])([CH3:36])([CH3:37])[CH3:38]

Participants

12

Reactant 5

HCID 11430Potassium CarbonateHCID 764292-ChlorothiazoleHCID 517044Potassium AcetateHCID 5462311BoronHCID 86605639HCID 86605639, compound

Product 1

HCID 68829901HCID 68829901, compoundYield 75.2%

Reagents, catalysts & solvents 6

HCID 178418397HCID 178418397, compoundCatalystHCID 178418807HCID 178418807, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolvent3×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl [4-(4-methylphenyl)-2-neopentyl-6-trifluoromethanesulfonyloxy-quinolin-3-yl]methylcarbamate (3.97 g, 7.0 mmol), boron bispinacolate (3.55 g, 14.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium-dichloromethane (1:1) complex (0.15 g, 0.21 mmol), potassium acetate (2.06 g, 21 mmol) and dimethyl sulfoxide (50 ml) was stirred under an argon atmosphere at 100° C. for 2 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and a mixture of the residue, 2-chlorothiazole (2.68 g, 14.0 mmol), tetrakis(triphenylphosphine)palladium (0.80 g, 0.7 mmol), potassium carbonate (2.90 g, 21 mmol), ethanol (5 ml), toluene (30 ml) and water (5 ml) was stirred under an argon atmosphere at 100° C. for 10 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give ethyl 2-[3-[[(tert-butoxycarbonyl)amino]methyl]-4-(4-methylphenyl)-2-neopentyl-6-quinolinyl]-1,3-thiazole-4-carboxylate (3.02 g, yield 75%) as white crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. stirringwas stirred under an argon atmosphere at 100° C. for 10 hrs
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-af786bb1b65c41e0ab1664708c76dd09
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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