Triphenylphosphine → HCID 56596286, compound

HRID 2368030Notes

Reaction equation

HRID 2368030 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16](=[O:19])[NH:17][N:18]=3)[CH:15]=2)=[CH:6][CH:5]=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[CH2:30][CH2:31]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[CH2:30][CH2:31][N:17]1[C:16](=[O:19])[N:14]2[CH:15]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:9][CH:8]=3)[CH:11]=[CH:12][C:13]2=[N:18]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 450906762-(2,6-Difluorophenyl)ethanolHCID 58044589HCID 58044589, compound

Product 1

HCID 56596286HCID 56596286, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(4-(Trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (50.0 mg, 0.169 mmol), 2-(2,6-difluorophenyl)ethanol (40.1 mg, 0.2535 mmol, 1.5 equiv.) and PPh3 (66.5 mg, 0.2535 mmol, 1.5 equiv.) were dissolved in THF (3 mL) under nitrogen atmosphere in a 50 mL round bottomed flask. This mixture was treated with diethyl azodicarboxylate (40% toluene solution, d=0.956, 0.12 mL, 0.2535 mmol, 1.5 equiv.) at room temperature. After stirring for 5 h, the mixture was directly loaded onto preparative HPLC. The HPLC purification gave compound 63 as colorless crystals (38.6 mg, 0.0887 mmol, 52.5%). LCMS (EI: 70 eV) 458 (M++Na), 436 (M++1). FTIR (ATR) 1701 (O═C).

Workup

  1. customThe HPLC purification

Sources & evidence

ORD record
ord-2be893ec31334924ba46af43df06ae7e
Source dataset
uspto-grants-2014_04
Patent number
US08703759B2

Reaction notes

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