C16H22F6IN2P → HCID 136401582, compound

HRID 2388158Notes

Reaction equation

HRID 2388158 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)=[N:13][O:12][C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].CC1C=C(C)N=C(C)C=1.CC1C([IH+:39])=C(C)N=C(C)C=1.F[P-](F)(F)(F)(F)F>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)=[N:13][O:12][C:9]2=[C:10]([I:39])[N:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 46863890C16H22F6IN2PHCID 136401499HCID 136401499, compound

Product 1

HCID 136401582HCID 136401582, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-chloro-phenyl)-4-hydroxy-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (377 mg, 1.18 mmole), bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate (1.22 g, 2.36 mmole), and dichloromethane (12 ml) was stirred at room temperature for 20 h before it was concentrated and purified by flash column chromatography on silica gel with a gradient of dichloromethane and hexanes to give the title compound as a white solid (440 mg); MS: (+) m/z 445.02 (M+H+).

Workup

  1. concentrationwas concentrated
  2. custompurified by flash column chromatography on silica gel with a gradient of dichloromethane and hexanes

Sources & evidence

ORD record
ord-c80364b3c8054797abe2423171d661eb
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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