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

HRID 1950137Notes

Reaction equation

HRID 1950137 reaction equation
COC1C=C2C(=CC=1)C=C(C1C=CN=CC=1N)C=C2.BrC1C=CC(OCCN2CCCCC2)=C(F)C=1.[F:37][C:38]1[CH:39]=[C:40]([NH:53][C:54]2[CH:55]=[N:56][CH:57]=[CH:58][C:59]=2[C:60]2[CH:69]=[CH:68][C:67]3[C:62](=[CH:63][CH:64]=[C:65]([O:70]C)[CH:66]=3)[CH:61]=2)[CH:41]=[CH:42][C:43]=1[O:44][CH2:45][CH2:46][N:47]1[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1>>[F:37][C:38]1[CH:39]=[C:40]([NH:53][C:54]2[CH:55]=[N:56][CH:57]=[CH:58][C:59]=2[C:60]2[CH:61]=[C:62]3[C:67](=[CH:68][CH:69]=2)[CH:66]=[C:65]([OH:70])[CH:64]=[CH:63]3)[CH:41]=[CH:42][C:43]=1[O:44][CH2:45][CH2:46][N:47]1[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]1

Participants

4

Reactant 3

HCID 230870721-(2-(4-Bromo-2-fluorophenoxy)ethyl)piperidineHCID 230871624-(6-Methoxynaphthalen-2-yl)pyridin-3-ylamineHCID 23087403[3-Fluoro-4-(2-piperidin-1-ylethoxy)phenyl][4-(6-methoxynaphthalen-2-yl)pyridin-3-yl]amine

Product 1

HCID 1361755766-{3-[3-Fluoro-4-(2-piperidin-1-ylethoxy)phenylamino]pyridin-4-yl}naphthalen-2-olYield 74.5%

Procedure

Synthesized from 4-(6-methoxynaphthalen-2-yl)pyridin-3-ylamine 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][4-(6-methoxynaphthalen-2-yl)pyridin-3-yl]amine (343 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (248 mg).

Sources & evidence

ORD record
ord-e64f7857c06745e497320b09e12c2fb2
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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