Tetrahydrofuran → Benzoxazole

HRID 2094409Notes

Reaction equation

HRID 2094409 reaction equation
ClC1C=NC=CC=1[C:4]([NH:6][C:7]1[CH:12]=[C:11](C(F)(F)F)[C:10](Cl)=[CH:9][C:8]=1[OH:18])=O.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>[O:18]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[CH:4]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 668805073-chloro-N-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamide

Product 1

HCID 9228Benzoxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 0.46 g of 3-chloro-N-[4-chloro-2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 5 ml of tetrahydrofuran and 0.38 g of triphenylphosphine, 0.63 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 to give 0.39 g of 6-chloro-2-(3-chloropyridin-4-yl)-5-trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 81”).

Workup

  1. additionwas added dropwise at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7ca9c55181ad4e0bb202e82b967f4f05
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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