Tetrahydrofuran → 5-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazole

HRID 884890Notes

Reaction equation

HRID 884890 reaction equation
[Cl:1][C:2]1[C:3]([C:18]([F:21])([F:20])[F:19])=[CH:4][C:5]([OH:17])=[C:6]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=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>[Cl:1][C:2]1[C:3]([C:18]([F:21])([F:20])[F:19])=[CH:4][C:5]2[O:17][C:9]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[N:8][C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66879747N-[5-chloro-2-hydroxy-4-trifluoromethylphenyl]isonicotinamide

Product 1

HCID 668802185-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazoleYield 21.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 0.55 g of N-[5-chloro-2-hydroxy-4-(trifluoromethyl)phenyl]isonicotinamide, 6 ml of tetrahydrofuran and 0.50 g of triphenylphosphine, 0.83 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for 1.5 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 0.11 g of 5-chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 78”).

Workup

  1. additionwas added dropwise at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washthe resultant crystals were washed with methanol

Sources & evidence

ORD record
ord-1580816c1c3e4c33a4397101fbca4275
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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