6-Methoxy-2-naphthaleneboronic acid → 4-Fluoro-2-(6-methoxynaphthalen-2-yl)phenylamine

HRID 2423615Notes

Reaction equation

HRID 2423615 reaction equation
COC1C=C2C(=CC=1)C=C(B(O)O)C=C2.FC(F)(F)S(OC1C=C(F)C=CC=1[N+]([O-])=O)(=O)=O.[F:34][C:35]1[CH:36]=[CH:37][C:38]([N+:53]([O-])=O)=[C:39]([CH:41]2[CH2:50][CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[C:46]([O:51][CH3:52])[CH:47]=3)[CH2:42]2)[CH:40]=1>>[F:34][C:35]1[CH:36]=[CH:37][C:38]([NH2:53])=[C:39]([C:41]2[CH:50]=[CH:49][C:48]3[C:43](=[CH:44][CH:45]=[C:46]([O:51][CH3:52])[CH:47]=3)[CH:42]=2)[CH:40]=1

Participants

4

Reactant 3

HCID 46416926-Methoxy-2-naphthaleneboronic acidHCID 230871615-Fluoro-2-nitrophenyl trifluoromethanesulfonateHCID 230875552-(5-Fluoro-2-nitrophenyl)-6-methoxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 230872044-Fluoro-2-(6-methoxynaphthalen-2-yl)phenylamineYield 95.4%

Procedure

Synthesized from (6-methoxynaphthalen-2-yl)boronic acid and 5-fluoro-2-nitrophenyl trifluoromethanesulfonate according to an analogous synthetic method to Example 24, 2-(5-fluoro-2-nitrophenyl)-6-methoxy-1,2,3,4-tetrahydronaphthalene (1.3 g) was used according to an analogous synthetic method to Example 22 to provide the title compound (1.1 g).

Sources & evidence

ORD record
ord-e996c15683b146bda87cc82419501581
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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