Tetrahydrofuran → 2-(3-Chloropyridin-4-yl)-5-(pentafluoroethyl)benzoxazole

HRID 884878Notes

Reaction equation

HRID 884878 reaction equation
[Cl:1][C:2]1[CH:24]=[N:23][CH:22]=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:8]=1[OH:20])=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>[Cl:1][C:2]1[CH:24]=[N:23][CH:22]=[CH:21][C:3]=1[C:4]1[O:20][C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:19])([F:18])[C:14]([F:16])([F:17])[F:15])=[CH:12][C:7]=2[N:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 866510493-chloro-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]isonicotinamide

Product 1

HCID 866510482-(3-Chloropyridin-4-yl)-5-(pentafluoroethyl)benzoxazoleYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 0.24 g of 3-chloro-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]isonicotinamide, 4 ml of tetrahydrofuran and 0.21 g of triphenylphosphine, 0.34 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for 1.8 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.19 g of 2-(3-chloropyridin-4-yl)-5-(pentafluoroethyl)benzoxazole (hereinafter, referred to as “active compound 66”).

Workup

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

Sources & evidence

ORD record
ord-7ecb181fa0504433a537d87dbfd821f6
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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