Triphenylphosphine → HCID 66644374, compound

HRID 1962976Notes

Reaction equation

HRID 1962976 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[N:6][CH:7]=1.[CH3:16][O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][N:21]=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[CH:25]=[CH:24][C:23]([O:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)=[N:9][O:10][C:11]=2[CH3:15])=[CH:22][N:21]=1)=[O:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4715126Methyl 5-hydroxypyridine-2-carboxylateHCID 66599256[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol

Product 1

HCID 66644374HCID 66644374, compoundYield 108.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol (854 mg, 4.1 mmol) in THF (40 mL) was added 5-hydroxy-pyridine-2-carboxylic acid methyl ester (691 mg, 4.5 mmol) and triphenylphosphine (1.61 g, 6.1 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (2.82 mL, 40% solution in toluene, 6.0 mmol) was added and the reaction mixture was stirred for 2 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 (1.53 g, 76%) as an off white solid. MS: m/e=344.0 [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-5901c3e98436476ea69edd6fb0bec122
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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