Triphenylphosphine → HCID 67495619, compound

HRID 2365222Notes

Reaction equation

HRID 2365222 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[N:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]([C:20]1[N:21]([CH3:26])[N:22]=[C:23](O)[CH:24]=1)=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:16][O:17][C:18]([C:20]1[N:21]([CH3:26])[N:22]=[C:23]([O:14][CH2:13][C:12]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:9]=[N:10][C:11]=2[CH3:15])[CH:24]=1)=[O:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19914681(1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methanolHCID 178498598HCID 178498598, compound

Product 1

HCID 67495619HCID 67495619, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-methanol (500 mg, 2 mmol) in THF (30 mL) was added 5-hydroxy-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (377 mg, 2 mmol) and triphenylphosphine (823 mg, 3 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (˜40% in toluene, 1.44 mL, 3 mmol) was added and the reaction mixture was stirred for 24 h at room temperature. Concentration and purification by chromatography (silica, 20 to 50% ethyl acetate in heptane and then 2% methanol in dichloromethane) afforded the title compound (671 mg, 81%) as a white solid. MS: m/e=346.1 [M+H]+.

Workup

  1. concentrationConcentration and purification by chromatography (silica, 20 to 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-8e3c5e7f7aa54f2280c46fc2941ee07c
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

Loading…