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

HRID 2094408Notes

Reaction equation

HRID 2094408 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12][C:13](=O)[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:4]([OH:21])[CH:3]=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:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5]2[N:12]=[C:13]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[O:21][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66880038N-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamide

Product 1

HCID 668817606-Chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazoleYield 69.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 1.01 g of N-[4-chloro-2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 10 ml of tetrahydrofuran and 0.92 g of triphenylphosphine, 1.53 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature, and the reaction mixture was stirred for two hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and the resultant crystals washed with methanol to give 0.66 g of 6-chloro-2-(pyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 80”).

Workup

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

Sources & evidence

ORD record
ord-fce5c64e1065445d9a1987355af1bddc
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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