1-{2-{2-Fluoro-4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]ethyl}phenoxy}ethyl}azepane → 6-{2-{2-[4-(2-Azepan-1-ylethoxy)-3-fluorophenyl]ethyl}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950311Notes

Reaction equation

HRID 1950311 reaction equation
FC1C=C(CCC2C=C(OC)C=CC=2C2CCC3C(=CC=C(OC)C=3)C2)C=CC=1O.Cl.ClCCN1CCCCCC1.[F:42][C:43]1[CH:58]=[C:57]([CH2:59][CH2:60][C:61]2[CH:66]=[C:65]([O:67]C)[CH:64]=[CH:63][C:62]=2[CH:69]2[CH2:78][CH2:77][C:76]3[C:71](=[CH:72][CH:73]=[C:74]([O:79]C)[CH:75]=3)[CH2:70]2)[CH:56]=[CH:55][C:44]=1[O:45][CH2:46][CH2:47][N:48]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1>>[N:48]1([CH2:47][CH2:46][O:45][C:44]2[CH:55]=[CH:56][C:57]([CH2:59][CH2:60][C:61]3[CH:66]=[C:65]([OH:67])[CH:64]=[CH:63][C:62]=3[CH:69]3[CH2:78][CH2:77][C:76]4[CH:75]=[C:74]([OH:79])[CH:73]=[CH:72][C:71]=4[CH2:70]3)=[CH:58][C:43]=2[F:42])[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1

Participants

4

Reactant 3

HCID 230871631-{2-{2-Fluoro-4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]ethyl}phenoxy}ethyl}azepaneHCID 24188283N-(2-chloroethyl)perhydroazepine hydrochlorideHCID 579345142-Fluoro-4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]ethyl}phenol

Product 1

HCID 579344946-{2-{2-[4-(2-Azepan-1-ylethoxy)-3-fluorophenyl]ethyl}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 61.9%

Procedure

Synthesized from 2-fluoro-4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]ethyl}phenol and 1-(2-chloroethyl)azepane hydrochloride according to an analogous synthetic method to Preparation Example 40, 1-{2-{2-fluoro-4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]ethyl}phenoxy}ethyl}azepane (203 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (119 mg).

Sources & evidence

ORD record
ord-cfaea96ca1854f4397e38a6188aab23c
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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