Tetrahydrofuran → HCID 58148278, compound

HRID 884899Notes

Reaction equation

HRID 884899 reaction equation
[F:1][C:2]1[CH:24]=[N:23][CH:22]=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1O)[C:12]([F:18])([F:17])[O:11][C:10]2([F:20])[F:19])=[O:5].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>[F:20][C:10]1([F:19])[C:9]2[C:13](=[CH:14][C:15]3[O:5][C:4]([C:3]4[CH:21]=[CH:22][N:23]=[CH:24][C:2]=4[F:1])=[N:6][C:7]=3[CH:8]=2)[C:12]([F:17])([F:18])[O:11]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66879858HCID 66879858, compound

Product 1

HCID 58148278HCID 58148278, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 1.46 g of 3-fluoro-N-(1,1,3,3-tetrafluoro-6-hydroxy-1,3-dihydroisobenzofuran-5-yl)isonicotinamide, 10 ml of tetrahydrofuran and 2.02 g of triphenylphosphine, 0.90 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature, and the reaction mixture was stirred for one hour. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.09 g of 5,5,7,7-tetrafluoro-2-(3-fluoropyridin-4-yl)-5,7-dihydro-furo[3′,4′:4,5]benzo[1,2-d]oxazole (hereinafter, referred to as “active compound 87”).

Workup

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

Sources & evidence

ORD record
ord-4ac7eda1f7c341d7b4f5e397ffe24cd9
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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