Water → Ethyl 2-(benzo[d]oxazol-2-yl)nicotinate

HRID 1400236Notes

Reaction equation

HRID 1400236 reaction equation
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([Sn](CCCC)(CCCC)[C:18]1[O:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1)CCC.O.CCOC(C)=O>CN(C=O)C.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[O:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=[C:18]1[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2796614Ethyl chloronicotinateHCID 37665862-(Tributylstannyl)-1,3-benzoxazole

Product 1

HCID 67540260Ethyl 2-(benzo[d]oxazol-2-yl)nicotinateYield 200.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 2-chloronicotinate (100 mg, 0.539 mmol), 2-(tributylstannyl)benzo[d]oxazole (314 mg, 0.539 mmol) and [1,1′-bis(diphenylphosphino) ferrocene]-dichloropalladium (II) (39.4 mg, 0.054 mmol) in DMF (2 mL) was heated to 110° C. for 1 h by applying microwave radiation to the mixture. The reaction was repeated on the same scale and the thus obtained reaction mixtures obtained were combined. Excess water and EtOAc were added. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and dried over MgSO4. Purification by flash column chromatography (EtOAc/DCM, gradient: 1-10% DCM) provided the title compound (290 mg, 90%);

Workup

  1. customthe thus obtained reaction mixtures
  2. customobtained
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. customPurification by flash column chromatography (EtOAc/DCM, gradient: 1-10% DCM)

Sources & evidence

ORD record
ord-8b32846cd97c4771ad22c5df00e11639
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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