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

HRID 2190764Notes

Reaction equation

HRID 2190764 reaction equation
[Cl:1][C:2]1[CH:22]=[N:21][CH:20]=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([S:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[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>[Cl:1][C:2]1[CH:22]=[N:21][CH:20]=[CH:19][C:3]=1[C:4]1[O:18][C:8]2[CH:9]=[CH:10][C:11]([S:13][C:14]([F:17])([F:16])[F:15])=[CH:12][C:7]=2[N:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66881883HCID 66881883, compound

Product 1

HCID 668809412-(3-Chloropyridin-4-yl)-5-(trifluoromethylthio)benzoxazoleYield 93.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 0.64 g of 3-chloro-N-[2-hydroxy-5-(trifluoromethylthio)phenyl]isonicotinamide, 6 ml of tetrahydrofuran and 0.53 g of triphenylphosphine, 0.87 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature and stirred for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.57 g of 2-(3-chloropyridin-4-yl)-5-(trifluoromethylthio)benzoxazole (hereinafter, referred to as “active compound 77”).

Workup

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

Sources & evidence

ORD record
ord-217cf416e9fb4b7394427bfdec83f486
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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