Cesium carbonate → HCID 58081253, compound

HRID 928454Notes

Reaction equation

HRID 928454 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[CH:7]=[CH:6]2.[O:14]1[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:16]=[CH:15]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(P(C2C(C3C=CC=CC=3)=CC=CC=2)C2CCCCC2)CC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][C:15]3[O:14][CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:16]=3)[CH:4]=2)[N:9]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 2763217Ethyl oxazole-4-carboxylateHCID 22081337HCID 22081337, compound

Product 1

HCID 58081253HCID 58081253, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(Chloromethyl)-2-methylquinoline (1.09 g, 5.69 mmol), Ethyl oxazole-4-carboxylate (1.00 g, 7.11 mmol), Cesium carbonate (3.7 g, 11.37 mmol), Palladium(II)acetate (64 mg, 0.284 mmol) and (2-Biphenyl)dicyclohexyl-phosphine (199 mg, 0.569 mmol) in dioxane (28 ml) was stirred at 100° C. over night. The reaction mixture was quenched with H2O/brine and extracted with EA (3×). The combined organic layers were dried over Na2SO4, filtered and evaporated under vacuum. The crude product was purified by flash-chromatography on silica gel (29 g), gradient of cyclohexane/EA (60 ml/min.) from 100/0 (2 min.) to 70/30 (25 min.) to afford pure Ethyl 2-((2-methylquinolin-6-yl)methyl)oxazole-4-carboxylate. MS (Method V) [M+H]+=297.1

Workup

  1. customThe reaction mixture was quenched with H2O/brine
  2. extractionextracted with EA (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe crude product was purified by flash-chromatography on silica gel (29 g), gradient of cyclohexane/EA (60 ml/min.) from 100/0 (2 min.) to 70/30 (25 min.)

Sources & evidence

ORD record
ord-f5946231f29b4a97a148b829ef5e2646
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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