Triphenylphosphine → Methyl 5-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylate

HRID 2365216Notes

Reaction equation

HRID 2365216 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH2:14][OH:15])=[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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH2:14][O:15][C:23]2[CH:24]=[C:20]([C:18]([O:17][CH3:16])=[O:19])[N:21]([CH3:26])[N:22]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67498408[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-methanolHCID 178498598HCID 178498598, compound

Product 1

HCID 67496027Methyl 5-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-methanol (290 mg, 1.4 mmol) in THF (30 mL) was added 5-hydroxy-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (218 mg, 1.4 mmol) and triphenylphosphine (477 mg, 1.82 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (641 μL, 3.5 mmol) was added and the reaction mixture was stirred for 16 h at room temperature. Concentration and purification by chromatography (silica, 20 to 50% ethyl acetate in heptane) afforded the title compound (483 mg, 100%) as a white solid. MS: m/e=346.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-396dddb6b5aa44a6a94bce2427b38b14
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

Loading…