Triphenylphosphine → 4-Chloro-7-fluoro-6-[2-(4-morpholinyl)ethoxy]-3-quinolinecarbonitrile

HRID 1837344Notes

Reaction equation

HRID 1837344 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[C:9]([OH:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[C:9]([O:12][CH2:48][CH2:49][N:50]3[CH2:55][CH2:54][O:53][CH2:52][CH2:51]3)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 234980764-Chloro-7-fluoro-6-hydroxy-3-quinolinecarbonitrile

Product 1

HCID 234980934-Chloro-7-fluoro-6-[2-(4-morpholinyl)ethoxy]-3-quinolinecarbonitrileYield 57%

Procedure

Following the procedure used to prepare Reference Example 14, reaction of 4-chloro-7-fluoro-6-hydroxy-3-quinolinecarbonitrile with triphenyl phosphine, diethyl azodicarboxylate and 4-(2-hydroxyethyl)morpholine provides 4-chloro-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile in 57% yield. An analytical sample is obtained by preparative thin layer chromatography eluting with 1% methanol in ethyl acetate, mp 163-164° C.

Workup

  1. customto prepare

Sources & evidence

ORD record
ord-bee9638fd0104905a80aadcd9ad69dd7
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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