1-(2-(4-Bromo-2-fluorophenoxy)ethyl)piperidine → 6-{2-[3-Fluoro-4-(2-piperidin-1-ylethoxy)phenylamino]-4-hydroxyphenyl}-5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950262Notes

Reaction equation

HRID 1950262 reaction equation
COC1C=CC(C2CCC3C(=CC=C(OC)C=3)C2(C)C)=C(N)C=1.BrC1C=CC(OCCN2CCCCC2)=C(F)C=1.[F:41][C:42]1[CH:43]=[C:44]([NH:57][C:58]2[CH:63]=[C:62]([O:64]C)[CH:61]=[CH:60][C:59]=2[CH:66]2[CH2:75][CH2:74][C:73]3[C:68](=[CH:69][CH:70]=[C:71]([O:76]C)[CH:72]=3)[C:67]2([CH3:79])[CH3:78])[CH:45]=[CH:46][C:47]=1[O:48][CH2:49][CH2:50][N:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1>>[F:41][C:42]1[CH:43]=[C:44]([NH:57][C:58]2[CH:63]=[C:62]([OH:64])[CH:61]=[CH:60][C:59]=2[CH:66]2[CH2:75][CH2:74][C:73]3[CH:72]=[C:71]([OH:76])[CH:70]=[CH:69][C:68]=3[C:67]2([CH3:79])[CH3:78])[CH:45]=[CH:46][C:47]=1[O:48][CH2:49][CH2:50][N:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1

Participants

4

Reactant 3

HCID 230870721-(2-(4-Bromo-2-fluorophenoxy)ethyl)piperidineHCID 230871285-Methoxy-2-(6-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineHCID 66627243[3-Fluoro-4-(2-piperidin-1-ylethoxy)phenyl][5-methoxy-2-(6-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

Product 1

HCID 579339626-{2-[3-Fluoro-4-(2-piperidin-1-ylethoxy)phenylamino]-4-hydroxyphenyl}-5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-olYield 84.6%

Procedure

Synthesized from 5-methoxy-2-(6-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalen-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-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (348 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (279 mg).

Sources & evidence

ORD record
ord-89ac505e5ccf4e0a8d54fd4d86993685
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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