2-Chloroethyldiisopropylammonium chloride → 6-{2-{2-[4-(2-Diisopropylaminoethoxy)-3-fluorophenyl]ethyl}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950312Notes

Reaction equation

HRID 1950312 reaction equation
FC1C=C(CCC2C=C(OC)C=CC=2C2CCC3C(=CC=C(OC)C=3)C2)C=CC=1O.Cl.ClCCN(C(C)C)C(C)C.[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]([CH:52]([CH3:54])[CH3:53])[CH:49]([CH3:51])[CH3:50]>>[CH:52]([N:48]([CH:49]([CH3:51])[CH3:50])[CH2:47][CH2:46][O:45][C:44]1[CH:55]=[CH:56][C:57]([CH2:59][CH2:60][C:61]2[CH:66]=[C:65]([OH:67])[CH:64]=[CH:63][C:62]=2[CH:69]2[CH2:78][CH2:77][C:76]3[CH:75]=[C:74]([OH:79])[CH:73]=[CH:72][C:71]=3[CH2:70]2)=[CH:58][C:43]=1[F:42])([CH3:54])[CH3:53]

Participants

4

Reactant 3

HCID 779422-Chloroethyldiisopropylammonium chlorideHCID 23087347{2-{2-Fluoro-4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]ethyl}phenoxy}ethyl}diisopropylamineHCID 579345142-Fluoro-4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]ethyl}phenol

Product 1

HCID 579341306-{2-{2-[4-(2-Diisopropylaminoethoxy)-3-fluorophenyl]ethyl}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 55.2%

Procedure

Synthesized from 2-fluoro-4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]ethyl}phenol and (2-chloroethyl)diisopropylamine hydrochloride according to an analogous synthetic method to Preparation Example 40, {2-{2-fluoro-4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]ethyl}phenoxy}ethyl}diisopropylamine (199 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (104 mg).

Sources & evidence

ORD record
ord-769b61f3319c45009993e29658da22bd
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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