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

HRID 1433946Notes

Reaction equation

HRID 1433946 reaction equation
COC1C=CC(C2C=CC3C(=CC=C(OC)C=3)C=2)=C(N)C=1.BrC1C=CC(OCCN2CCCCC2)=C(F)C=1.[F:39][C:40]1[CH:41]=[C:42]([NH:55][C:56]2[CH:61]=[C:60]([O:62]C)[CH:59]=[CH:58][C:57]=2[C:64]2[CH:73]=[CH:72][C:71]3[C:66](=[CH:67][CH:68]=[C:69]([O:74]C)[CH:70]=3)[CH:65]=2)[CH:43]=[CH:44][C:45]=1[O:46][CH2:47][CH2:48][N:49]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1>>[F:39][C:40]1[CH:41]=[C:42]([NH:55][C:56]2[CH:61]=[C:60]([OH:62])[CH:59]=[CH:58][C:57]=2[C:64]2[CH:65]=[C:66]3[C:71](=[CH:72][CH:73]=2)[CH:70]=[C:69]([OH:74])[CH:68]=[CH:67]3)[CH:43]=[CH:44][C:45]=1[O:46][CH2:47][CH2:48][N:49]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1

Participants

4

Reactant 3

HCID 230870721-(2-(4-Bromo-2-fluorophenoxy)ethyl)piperidineHCID 230875115-Methoxy-2-(6-methoxynaphthalen-2-yl)phenylamineHCID 66626121[3-Fluoro-4-(2-piperidin-1-ylethoxy)phenyl][5-methoxy-2-(6-methoxynaphthalen-2-yl)phenyl]amine

Product 1

HCID 579342386-{2-[3-Fluoro-4-(2-piperidin-1-ylethoxy)phenylamino]-4-hydroxyphenyl}naphthalen-2-olYield 71.8%

Procedure

Synthesized from 5-methoxy-2-(6-methoxynaphthalen-2-yl)phenylamine and 1-[2-(4-bromo-2-fluorophenoxy)ethyl]piperidine according to an analogous synthetic method to Example 116, [3-fluoro-4-(2-piperidin-1-ylethoxy)phenyl][5-methoxy-2-(6-methoxynaphthalen-2-yl)phenyl]amine (425 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (288 mg).

Sources & evidence

ORD record
ord-118f5b7d521342c6a37d2bd43dd0f4db
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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