Abstract
A practical and efficient process for the synthesis in good yield of 2-amino-4-(methoxycarbonyl)phenylboronic acid hydrochloride from p-bromo toluene has been developed via borylation, oxidation, nitration, esterification and hydrogenation.
Keywords
References
1.
Snieckus V.
, Med. Res. Rev. , 1999 , 19 , 342 .
2.
Ishiyama T.
, and
Miyaura N.
, Chem. Rev. , 2004 , 104 , 271 .
3.
Hall D.G.
, Boronic acids: preparation and applications in organic synthesis, medicine and materials , 2nd edn. Wiley-VCH : Weinheim , 2011 .
4.
Pierre F.
,
Chua P.C.
,
Brien S.E.
,
Jain A.S.
,
Bourbon P.
,
Haddach M.
,
Michaux J.
,
Nagasawa J.
,
Schwaebe M.K.
,
Stefan E.
,
Vialettes A.
,
Whitten J.P.
,
Chen T.K.
,
Darjania L.
,
Stansfield R.
,
Anderes K.
,
Bliesath J.
,
Drygin D.
,
Ho C.
,
Omori M.
,
Proffitt C.
,
Streiner N.
,
Trent K.
,
Rice W.G.
, and
Ryckman D.M.
, J. Med. Chem. , 2011 , 54 , 635 .
5.
Percec V.
,
Won B.C.
,
Peterca M.
, and
Heiney P.A.
, J. Am. Chem. Soc. , 2007 , 129 , 11265 .
6.
Anderes K.
,
Bourbon P.
,
Darjania L.
,
Haddach M.
,
Pierre F.
,
Rice W.G.
,
Ryckman D.M.
,
Schwaebe M.K.
,
Siddiqui J.A.
,
Stansfield R.
,
Stefan E.
, and
Streiner N.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 1687 .
7.
Shi C.
,
Xiong Z.M.
,
Chittepu P.
,
Aldrich C.C.
,
Ferguson D.M.
,
Ohlfest J.R.
, and
Ferguson D.M.
, ACS Med. Chem. Lett. , 2012 , 3 , 501 .
8.
Hodgetts K.J.
, and
Kershaw M.T.
, Org. Lett. , 2003 , 5 , 2911 .
9.
Chua P.C.
,
Haddach M.
,
Nagasawa J.Y.
,
Pierre F.
, and
Whitten J.P.
, Patent, US2009/239859, 2009.
10.
Chan K.S.
,
Zhou X.A.
,
Au M.T.
, and
Tam C.Y.
, Tetrahedron , 1995 , 51 , 3129 .
11.
Matsubara H.
,
Seto K.J.
,
Tahara T.
, and
Takahashi S.
, Bull. Chem. Soc. Jpn , 1989 , 62 , 3896 .
12.
Soloway A.H.
, J. Am. Chem. Soc. , 1959 , 81 , 3017 .