Abstract
Palladium-catalyzed Negishi cross-coupling of 5-1-(4-fluorophenyl)indolylzinc
chloride with N -methyl-halopyrazoles, bromopyridines
and bromopyrimidines in gram scale gave the corresponding cross-coupled
products in 38-85% yield.
Key words
indoles - Negishi reaction - Stille reaction - cross-coupling - palladium
References 1 Current address: Medicinal Chemistry
Research, Novo Nordisk A/S, Novo Nordisk Park, 2760 Måløv,
Denmark.
2
Perregaard J.
Arnt J.
Bøgesø KP.
Hyttel J.
Sanchez C.
J. Med. Chem.
1992,
35:
1092
3
Perregaard J.
Andersen K.
Hyttel J.
Sanchez C.
J. Med. Chem.
1992,
35:
4813
4
Andersen K.
Liljefors T.
Hyttel J.
Perregaard J.
J. Med. Chem.
1996,
39:
3723
5
Carbonnelle A.-C.
Zamora EG.
Beugelmans R.
Roussi G.
Tetrahedron Lett.
1998,
39:
4467
6
Yang Y.
Martin AR.
Synth. Commun.
1992,
22:
1757
7
Nielsen SF.
Peters D.
Axelsson O.
Synth.
Commun.
2000,
30:
3501
8
Pearce BC.
Synth.
Commun.
1992,
22:
1627
9
Hudkins RL.
Diebold JL.
Marsh FD.
J. Org. Chem.
1995,
60:
6218
10
Jensen J.
Skjærbæk N.
Vedsø P.
Synthesis
2001,
128
11
Yang Y.
Martin AR.
Nelson DL.
Regan J.
Heterocycles
1992,
34:
1169
12
Yang Y.
Martin AR.
Heterocycles
1992,
34:
1395
13
Chu L.
Fisher MH.
Goulet MT.
Wyvratt MJ.
Tetrahedron Lett.
1997,
38:
3871
14
Baston E.
Hartmann RW.
Bioorg. Med. Chem.
Lett.
1999,
9:
1601
15
Meng CQ.
Rakhit S.
Lee DKH.
Kamboj R.
McCallum KL.
Mazzocco L.
Dyne K.
Slassi A.
Bioorg. Med. Chem. Lett.
2000,
10:
903
16 We performed Negishi cross-coupling
reactions in 21 g (73 mmol) scale without encountering any problems.
See preparation of 11 .
17
Takami H.
Koshimura H.
Kumazawa T.
Heterocycles
1999,
51:
1119
18
Amat M.
Hadida S.
Sathyanarayana S.
Bosch J.
J. Org. Chem.
1994,
59:
10
19
Moyer MP.
Shiurba JF.
Rapoport H.
J.
Org. Chem.
1986,
51:
5106
20
Bridges AJ.
Lee A.
Maduakor EC.
Schwartz CE.
Tetrahedron Lett.
1992,
33:
7499
21
Bridges AJ.
Lee A.
Maduakor EC.
Schwartz CE.
Tetrahedron Lett.
1992,
33:
7495
22
Krizan TD.
Martin JC.
J. Am. Chem. Soc.
1983,
105:
6155
23
Felding J.
Uhlmann P.
Kristensen J.
Vedsø P.
Begtrup M.
Synthesis
1998,
1181
24
Katrizky A.
Lue P.
Akutagawa K.
Tetrahedron
1989,
45:
4253
25
Effenberger F.
Krebs A.
J. Org. Chem.
1984,
49:
4687