1-(2-(4-Bromo-2-fluorophenoxy)ethyl)piperidine → 6-{4-Fluoro-2-[3-fluoro-4-(2-piperidin-1-ylethoxy)phenylamino]phenyl}naphthalen-2-ol

HRID 2423705Notes

Reaction equation

HRID 2423705 reaction equation
FC1C=CC(C2C=CC3C(=CC=C(OC)C=3)C=2)=C(N)C=1.BrC1C=CC(OCCN2CCCCC2)=C(F)C=1.[F:38][C:39]1[CH:40]=[CH:41][C:42]([C:62]2[CH:71]=[CH:70][C:69]3[C:64](=[CH:65][CH:66]=[C:67]([O:72]C)[CH:68]=3)[CH:63]=2)=[C:43]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([O:52][CH2:53][CH2:54][N:55]3[CH2:60][CH2:59][CH2:58][CH2:57][CH2:56]3)=[C:48]([F:61])[CH:47]=2)[CH:44]=1>>[F:38][C:39]1[CH:40]=[CH:41][C:42]([C:62]2[CH:63]=[C:64]3[C:69](=[CH:70][CH:71]=2)[CH:68]=[C:67]([OH:72])[CH:66]=[CH:65]3)=[C:43]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([O:52][CH2:53][CH2:54][N:55]3[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60]3)=[C:48]([F:61])[CH:47]=2)[CH:44]=1

Participants

4

Reactant 3

HCID 230870721-(2-(4-Bromo-2-fluorophenoxy)ethyl)piperidineHCID 230872415-Fluoro-2-(6-methoxynaphthalen-2-yl)phenylamineHCID 66627148[5-Fluoro-2-(6-methoxynaphthalen-2-yl)phenyl][3-fluoro-4-(2-piperidin-1-ylethoxy)phenyl]amine

Product 1

HCID 579343206-{4-Fluoro-2-[3-fluoro-4-(2-piperidin-1-ylethoxy)phenylamino]phenyl}naphthalen-2-olYield 96.6%

Procedure

Synthesized from 5-fluoro-2-(6-methoxynaphthalen-2-yl)phenylamine and 1-[2-(4-bromo-2-fluorophenoxy)ethyl]piperidine according to an analogous synthetic method to Example 116, [5-fluoro-2-(6-methoxynaphthalen-2-yl)phenyl][3-fluoro-4-(2-piperidin-1-ylethoxy)phenyl]amine (406 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (381 mg).

Sources & evidence

ORD record
ord-4650a15c52e444d8bfc50d514121329b
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

Loading…