Triphenylphosphine → 5-[3-(4-Fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

HRID 1962985Notes

Reaction equation

HRID 1962985 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:23]([O:25][C:26]([C:28]1[CH:33]=[CH:32][C:31](O)=[CH:30][N:29]=1)=[O:27])[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:23]([O:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([O:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][O:10][C:11]=2/[CH:15]=[CH:16]/[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:30][N:29]=1)=[O:27])[CH3:24]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 231458205-Hydroxypyridine-2-carboxylic acid ethyl esterHCID 66643905[3-(4-Fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-yl]-methanol

Product 1

HCID 666444395-[3-(4-Fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl esterYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [3-(4-fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-yl]-methanol (4.0 g, 13.5 mmol) and 5-hydroxy-pyridine-2-carboxylic acid ethyl ester (2.49 g, 14.9 mmol) in THF (130 mL) under argon was added triphenylphosphine (5.49 g, 20.31 mmol). Diethyl azodicarboxylate (9.3 mL, 20.31 mmol) was then added dropwise. After 3 h the reaction mixture was concentrated then purified by chromatography (silica, 10 to 40% ethyl actetate in heptane) afforded the title compound (2.85 g, 47%) as a white solid. MS: m/e=445.4 [M+H]+.

Workup

  1. concentrationAfter 3 h the reaction mixture was concentrated
  2. customthen purified by chromatography (silica, 10 to 40% ethyl actetate in heptane)

Sources & evidence

ORD record
ord-ba0f546b3b51411a9811f11121133a2c
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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