Water → Ethyl 2-(2-phenyloxazol-4-yl)nicotinate

HRID 1400239Notes

Reaction equation

HRID 1400239 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1Cl)[CH3:2].[C:13]1([C:19]2[O:20][CH:21]=[C:22](B3OC(C)(C)C(C)(C)O3)[N:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd-3](Cl)(Cl)C1C(Cl)=CC=CN=1)(C)C>[C:13]1([C:19]2[O:20][CH:21]=[C:22]([C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:4]([O:3][CH2:1][CH3:2])=[O:12])[N:23]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2796614Ethyl chloronicotinateHCID 115581042-Phenyl-1,3-oxazole-4-boronic acid, pinacol ester

Product 1

HCID 67540589Ethyl 2-(2-phenyloxazol-4-yl)nicotinateYield 42%

Reagents, catalysts & solvents 2

HCID 178439029HCID 178439029, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

[1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (22 mg, 0.032 mmol) was added to a mixture of ethyl-2-chloronicotinate (120 mg, 0.647 mmol) and 2-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxazole (220 mg, 0.811 mmol) in dioxane (5 mL). After the addition of K2CO3 (402 mg, 2.910 mmol) the reaction mixture was heated at 65° C. for 4 h and then allowed to cool to room temperature. Water was added and the mixture was extracted with EtOAc. The combined organic layers were washed with water and dried (MgSO4). Purification of the thus obtained raw product by flash column chromatography (dichloromethane/EtOAc, gradient 5-10% EtOAc) provided the title compound (80 mg, 42%); ESI-MS [M+H+]=295.1.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. customPurification of the
  6. customthus obtained raw product by flash column chromatography (dichloromethane/EtOAc, gradient 5-10% EtOAc)

Sources & evidence

ORD record
ord-2f4f9d04cb6d4f4db6cd9ea6bbb516ca
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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