Tetrahydrofuran → 2-(Pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole

HRID 1913651Notes

Reaction equation

HRID 1913651 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[N:18]1[CH:17]=[CH:16][C:15]([C:14]2[O:21][C:2]3[CH:7]=[CH:6][C:5]([S:8][C:9]([F:10])([F:11])[F:12])=[CH:4][C:3]=3[N:13]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 66880242HCID 66880242, compound

Product 1

HCID 668807602-(Pyridin-4-yl)-5-(trifluoromethylthio)benzoxazoleYield 26.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 0.69 g of N-[2-hydroxy-5-(trifluoromethylthio)phenyl]isonicotinamide, 9 ml of tetrahydrofuran, and 0.63 g of triphenylphosphine, 1.05 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature and stirred for three hours. To the mixture, 0.21 g of triphenylphosphine and 0.35 g of 40% toluene solution of diethyl azodicarboxylate were added. The reaction mixture was stirred for further two hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and the resultant crystals were washed with methanol to give 0.17 g of 2-(pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole (hereinafter, referred to as “active compound 76”).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringThe reaction mixture was stirred for further two hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe resultant crystals were washed with methanol

Sources & evidence

ORD record
ord-f0ec5890c08c41028c7844a793c311f6
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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