4-(Pyridin-3-Yloxy)Aniline → 7-Fluoro-6-methoxy-4-[4-(pyridin-3-yloxy)phenylamino]-quinoline-3-carbonitrile

HRID 499107Notes

Reaction equation

HRID 499107 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH:18]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[F:14][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:30][C:27]3[CH:26]=[CH:25][C:24]([O:23][C:19]4[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=4)=[CH:29][CH:28]=3)=[C:3]([C:15]#[N:16])[CH:4]=[N:5]2)=[CH:10][C:9]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 31596314-(Pyridin-3-Yloxy)AnilineHCID 10176127Pyridinium chlorideHCID 121507034-Chloro-7-fluoro-6-methoxy-3-quinolinecarbonitrile

Product 1

HCID 684604217-Fluoro-6-methoxy-4-[4-(pyridin-3-yloxy)phenylamino]-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Following the procedure of Example 1, a mixture of 635.4 mg (2.68 mmol) 4-chloro-7-fluoro-6-methoxy-quinoline-3-carbonitrile, 500 mg (2.81 mmol) of 4-(pyridin-3-yloxy)phenylamine and 309.8 mg (2.68 mmol) of pyridine hydrochloride are refluxed in 2-ethoxyethanol (27 mL) at 100° C. for 12 hours to yield 7-fluoro-6-methoxy-4-[4-(pyridin-3-yloxy)-phenylamino]-quinoline-3-carbonitrile as an off-white solid, mp 235-236° C.

Sources & evidence

ORD record
ord-9f30465e24a942518f7268ceb8e23b80
Source dataset
uspto-grants-2010_08
Patent number
US07767671B2

Reaction notes

Loading…