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

HRID 1920934Notes

Reaction equation

HRID 1920934 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[S:23][N:22]=[C:21](O)[CH: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[S:23][N:22]=[C:21]([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:20]=1)=[O:18]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66643722(5-Methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanolHCID 178498604HCID 178498604, compound

Product 1

HCID 674920473-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl esterYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol (360 mg, 1.9 mmol) in THF (10 mL) was added 3-hydroxy-isothiazole-5-carboxylic acid methyl ester (300 mg, 1.9 mmol) and triphenylphosphine (594 mg, 1.9 mmol) at 0° C. under an argon atmosphere. Then diethyl azodicarboxylate (˜40% in toluene, 0.95 mL, 1.9 mmol) was added and the reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:4) afforded the title compound (350 mg, 56%) as a white solid. MS: m/e=332.2 [M+H]+.

Workup

  1. concentrationConcentration and purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:4)

Sources & evidence

ORD record
ord-13eea28fd970406cbcdbad8d7e9a86a0
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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