Triphenylphosphine → 5-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid methyl ester

HRID 1962957Notes

Reaction equation

HRID 1962957 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:3]=1[CH2:13][OH:14].[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][N:20]=1)=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:21][N:20]=1)=[O:18]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4715126Methyl 5-hydroxypyridine-2-carboxylateHCID 66643722(5-Methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol

Product 1

HCID 666445115-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid methyl esterYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol (100 mg, 0.53 mmol) in THF (5 mL) was added 5-hydroxy-pyridine-2-carboxylic acid methyl ester (89 mg, 0.58 mmol) and triphenylphosphine (207 mg, 0.79 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (362 μL, 40% solution in toluene, 0.79 mmol) was added and the reaction mixture was stirred for 3 h at room temperature. The reaction mixture was evaporated and then purified by chromatography (silica, heptane:ethyl acetate=100:0 to 2:3) to afford the title compound (78 mg, 44%) as a white solid. MS: m/e=326.1 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by chromatography (silica, heptane:ethyl acetate=100:0 to 2:3)

Sources & evidence

ORD record
ord-a0388521be944a1b8d573dcde05e74c4
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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