Tetrahydrofuran → HCID 86651050, compound

HRID 1913642Notes

Reaction equation

HRID 1913642 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[NH:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=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>[N:23]1[CH:24]=[CH:25][C:20]([C:19]2[O:26][C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:17])([C:13]([F:14])([F:16])[F:15])[C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=3[N:18]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86651051HCID 86651051, compound

Product 1

HCID 86651050HCID 86651050, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 0.79 g of N-[2-hydroxy-5-(heptafluoroisopropyl)phenyl]isonicotinamide, 8 ml of tetrahydrofuran and 0.60 g of triphenylphosphine, 0.99 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for 2.3 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-(pyridin-4-yl)-5-(heptafluoroisopropyl)benzoxazole (hereinafter, referred to as “active compound 67”).

Workup

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

Sources & evidence

ORD record
ord-44fa2c32d13148139e9a809f9b0157ba
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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