5-Fluoro-2-nitrophenyl trifluoromethanesulfonate → 4-Fluoro-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine

HRID 1950055Notes

Reaction equation

HRID 1950055 reaction equation
FC(F)(F)S(OC1C=C(F)C=CC=1[N+]([O-])=O)(=O)=O.COC1C=C2C(=CC=1)C=C([Sn](C)(C)C)CC2.[F:35][C:36]1[CH:37]=[CH:38][C:39]([N+:54]([O-])=O)=[C:40]([C:42]2[CH2:43][CH2:44][C:45]3[C:50]([CH:51]=2)=[CH:49][CH:48]=[C:47]([O:52][CH3:53])[CH:46]=3)[CH:41]=1>>[F:35][C:36]1[CH:37]=[CH:38][C:39]([NH2:54])=[C:40]([CH:42]2[CH2:43][CH2:44][C:45]3[C:50](=[CH:49][CH:48]=[C:47]([O:52][CH3:53])[CH:46]=3)[CH2:51]2)[CH:41]=1

Participants

4

Reactant 3

HCID 230871615-Fluoro-2-nitrophenyl trifluoromethanesulfonateHCID 23087176(6-Methoxy-3,4-dihydronaphthalen-2-yl)trimethyltinHCID 230872603-(5-Fluoro-2-nitrophenyl)-7-methoxy-1,2-dihydronaphthalene

Product 1

HCID 230874154-Fluoro-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineYield 79.7%

Procedure

Synthesized from 5-fluoro-2-nitrophenyl trifluoromethanesulfonate and (6-methoxy-3,4-dihydronaphthalen-2-yl)trimethyltin according to an analogous synthetic method to Preparation Example 77, 3-(5-fluoro-2-nitrophenyl)-7-methoxy-1,2-dihydronaphthalene (396 mg) was used according to an analogous synthetic method to Example 30 to provide the title compound (286 mg).

Sources & evidence

ORD record
ord-4c63aa568ca54fa8b0459bfbdd00bae2
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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