Tetrahydrofuran → HCID 86651050, compound

HRID 2094395Notes

Reaction equation

HRID 2094395 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-579625aa43e145e2a9fb7d98da8d2f41
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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