Triphenylphosphine → HCID 66738064, compound

HRID 1966306Notes

Reaction equation

HRID 1966306 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][N:9]=[C:8]([I:12])[C:7]2=[O:13].[CH3:14][O:15][C:16]([CH3:21])([CH3:20])[CH2:17][CH2:18]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH2:18][CH2:17][C:16]([O:15][CH3:14])([CH3:21])[CH3:20])[N:9]=[C:8]([I:12])[C:7]2=[O:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 62118MethoxymethylbutanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66738315HCID 66738315, compound

Product 1

HCID 66738064HCID 66738064, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 0.72 g of 8-fluoro-3-iodocinnolin-4(1H)-one and 0.48 ml of 3-methoxy-3-methylbutan-1-ol in 20 ml of THF is cooled to 5° C., 0.97 g of triphenylphosphine is added and then 0.65 g of diethyl azodicarboxylate is slowly added, and the mixture is left stirring overnight at AT. The reaction mixture is concentrated under vacuum and the residue is chromatographed on silica gel, elution being carried out with the cyclohexane/AcOEt mixture (75/25; v/v) and then with AcOEt. The expected compound is obtained.

Workup

  1. waitthe mixture is left
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. customthe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-126ef527c6e640929ab564b37f60afd5
Source dataset
uspto-grants-2013_04
Patent number
US08420651B2

Reaction notes

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