4464
A. van den Hoogenband et al. / Tetrahedron Letters 48 (2007) 4461–4465
A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Garaliene, V.;
Farraguia, G.; Masotti, L. Bioorg. Med. Chem. Lett. 2004,
2, 1121–1128; Lin, N.; Xia, P.; Kovar, P.; Park, C.; Chen,
Z.; Zhang, H.; Rosenberg, S. H.; Sham, H. L. Bioorg.
Med. Chem. Lett. 2006, 16, 421–426.
009431, 2006; Chem. Abstr. 2006, 144, 170991; (b) De
Lange, B.; Lamberts-Verstappen, M. H.; Schieder-van de
Vondervoort, L.; Sereinig, N.; De Rijk, R.; De Vries, A.
H. M.; De Vries, J. G. Synlett 2006, 3105–3109.
23. Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128,
8742–8743.
1
1
0. (a) McDermott, M. C.; Stephenson, G. R.; Hughes, D. L.;
Walkington, A. J. Org. Lett. 2006, 8, 2917–2920; (b)
Overman, L. E.; Watson, D. A. J. Org. Chem. 2006, 71,
24. Selected analytical data for compounds 4–7: Compound 4:
1
3
H NMR (400 MHz, CDCl ): d 1.32–1.42 (m, 2H), 1.85–
2
600–2608; (c) Madin, A.; O’Donnell, J.; Oh, T.; Old, D.
W.; Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 2005,
27, 18054–18065; (d) Busacca, C. A.; Grossbach, D.;
1.92 (m, 2H), 2.06–2.14 (m, 2H), 2.69–2.76 (m, 2H), 3.45
(s, 2H), 3.79–3.89 (m, 1H), 3.99 (s, 2H), 5.14 (br d,
J = 8 Hz, 1H), 7.03 (t, J = 8 Hz, 1H), 7.21–7.32 (m, 5H),
1
1
Campbell, S. J.; Dong, D.; Eriksson, M. C.; Harris, R. E.;
Jones, P. J.; Kim, J. Y.; Lorentz, J. C.; McKellop, K. B.;
O’Brien, E. M.; Qiu, F.; Simpson, R. D.; Smith, L.; So, R.
C.; Spinelli, E. M.; Vitous, J.; Zavattaro, C. J. Org. Chem.
7.57 (d, J = 8 Hz, 2H). Compound 5: H NMR (400 MHz,
CDCl
3
): d 4.20 (s, 2H), 7.05–7.13 (m, 3H), 7.30 (t,
J = 8 Hz, 2H), 7.46 (d, J = 8 Hz, 2H), 7.62 (d, J = 8 Hz,
1
3
2H). Compound 6: H NMR (400 MHz, CDCl ): d 4.23 (s,
2
004, 69, 5187–5195; (e) Harayama, T.; Toko, H.;
Nishioka, H.; Abe, H.; Takeuchi, Y. Heterocycles 2003,
9, 541–546.
1. (a) Arao, T.; Kondo, K.; Aoyama, T. Tetrahedron Lett.
006, 47, 1417–1420; (b) Bignan, G. C.; Battista, K.;
2H), 7.07 (t, J = 8 Hz, 1H), 7.46 (br d, J = 7 Hz, 2H), 7.61
(d, J = 8 Hz, 2H), 7.87 (br s, 1H), 8.49 (d, J = 7 Hz, 2H).
1
5
Compound 7: H NMR (400 MHz, CDCl ): d 1.32 (s, 9H),
3
1
3.94 (s, 2H), 5.15 (br s, 1H), 7.01 (t, J = 8 Hz, 1H), 7.57 (d,
J = 8 Hz, 2H).
2
Connolly, P. J.; Orsini, M. J.; Liu, J.; Middleton, S. A.;
Reitz, A. B. Bioorg. Med. Chem. Lett. 2005, 15, 5022–
25. General procedure for the preparation of compounds 3
and 8–11 (Table 1): A dried 50 ml, three-necked reaction
vessel was charged with anhydrous and degassed NMP
(10 ml), followed by the addition of CuCl (10 mg,
0.1 mmol) and acetylacetonate (25 mg, 0.25 mmol). The
mixture was magnetically stirred under a nitrogen atmo-
sphere at room temperature until a clear dark solution was
obtained. After adding the N-substituted 2,6-dibromo-
phenylacetamide (1 mmol) and K CO (690 mg, 5 mmol),
5026; (c) Trost, M. B.; Frederiksen, M. U. Angew. Chem.,
Int. Ed. 2005, 44, 308–310; (d) Zhang, T. Y.; Zhang, H.
Tetrahedron Lett. 2002, 43, 1363–1365; (e) Zhang, T. Y.;
Zhang, H. Tetrahedron Lett. 2002, 43, 193–195; (f) Lee, S.;
Hartwig, J. F. J. Org. Chem. 2001, 66, 3402–3415.
1
1
1
2. Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003,
1
24, 12084–12085.
3. Pinto, A.; Neuville, L.; Retailleau, P.; Zhu, J. Org. Lett.
006, 8, 4927–4930.
2
3
the reaction mixture was heated in a pre-heated oil bath at
85 °C until the starting compound (1, 4–7) had disap-
peared (LCMS, TLC monitoring: CH Cl /MeOH =
2
4. Van den Hoogenband, A.; Den Hartog, J. A. J.; Lange, J.
2
2
H. M.; Terpstra, J. W. Tetrahedron Lett. 2004, 45, 8535–
97.5:2.5 (v/v), CH Cl /MeOH = 99:1 (v/v), CH Cl /ace-
2 2 2 2
8537.
2 2
tone = 9:1 (v/v) or CH Cl , depending on the starting
1
1
5. Buchwald, S. L.; Yang, B. H. Org. Lett. 1999, 1, 35–37.
6. Buchwald, S. L.; Nguyen, H. N.; Huang, X. J. Am. Chem.
Soc. 2003, 125, 11818–11819.
material). The reaction mixture was allowed to attain
room temperature. A solution of NH Cl in water and
4
ethyl acetate was added. The organic layer was separated,
1
7. (a) Kalinski, C.; Umkehrer, M.; Ross, G.; Kolb, J.;
Burdack, C.; Hiller, W. Tetrahedron Lett. 2006, 47, 3423–
4
extracted with water and dried over MgSO , filtered and
concentrated in vacuo. The crude product obtained was
further purified by flash chromatography (silica gel 60
(0.040–0.063 mm, Merck)) with the appropriate eluent.
3426; (b) Kitamura, Y.; Hashimoto, A.; Yoshikawa, S.;
Odaira, J.; Furuta, T.; Kan, T.; Tanaka, K. Synlett 2006,
1
15–117; (c) Turner, N. J.; Poondra, R. R. Org. Lett. 2005,
26. Selected analytical data for compounds 3 and 8–11:
1
7, 863–866.
Compound 3: H NMR (400 MHz, CDCl
3
): d 3.20 (s,
1
1
8. Van den Hoogenband, A.; Lange, J. H. M.; Iwema-
Bakker, W. I.; Den Hartog, J. A. J.; Van Schaik, J.;
Feenstra, R. W.; Terpstra, J. W. Tetrahedron Lett. 2006,
3H), 3.48 (s, 2H), 6.73–6.78 (m, 1H), 7.16–7.19 (m, 2H).
C NMR (100 MHz, CDCl /DMSO = 3:4 (v/v)): d 26.19,
3
36.52, 107.19, 118.08, 124.45, 125.17, 129.49, 146.16,
13
47, 4361–4364.
172.83. HRMS (ES+): calcd for C H BrNO (M+H)
9
9
1
9. (a) Lange, J. H. M.; Hofmeyer, L. J. F.; Hout, F. A. S.;
Osnabrug, S. J. M.; Verveer, P. C.; Kruse, C. G.; Feenstra,
R. W. Tetrahedron Lett. 2002, 43, 1101–1104; (b) Van
Berkel, S. S.; Van den Hoogenband, A.; Terpstra, J. W.;
Tromp, M.; Van Leeuwen, P. W. N. M.; Van Strijdonck,
G. P. F. Tetrahedron Lett. 2004, 45, 7659–7662; (c) Kuil,
M.; Bekedam, E. K.; Visser, G. M.; Van den Hoogenband,
A.; Terpstra, J. W.; Kamer, P. C. J.; Van Leeuwen, P. W.
N. M.; Van Strijdonck, G. P. F. Tetrahedron Lett. 2005,
225.9868; found 225.9861. Compound 8: H NMR
(400 MHz, CDCl ): d 1.66 (br d, J = 12 Hz, 2H), 2.13
3
(br t, J = 12 Hz, 2H), 2.36–2.48 (m, 2H), 3.01 (br d,
J = 12 Hz, 2H), 3.46 (s, 2H), 3.56 (s, 2H), 4.26–4.35 (m,
1H), 7.09–7.16 (m, 3H), 7.25–7.29 (m, 1H), 7.31–7.37 (m,
1
3
3
4H). C NMR (100 MHz, CDCl /DMSO = 3:4 (v/v)): d
27.67, 36.84, 50.23, 52.65, 62.18, 108.51, 118.46, 124.03,
125.42, 126.76, 128.01, 128.65, 129.30, 138.36, 144.82,
172.74. HRMS (ES+): calcd for C20
385.0915; found 385.0925. Compound 9: H NMR
H
2
22BrN1 O M+H
46, 2405–2409.
2
0. Some selected literature references: (a) Corbet, J. P.;
Mignani, G. Chem. Rev. 2006, 106, 2651–2710; (b) Frlan,
R.; Kikelj, D. Synthesis 2006, 2271–2285; (c) Beletskaya, I.
P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337–
(400 MHz, CDCl ): d 3.67 (s, 2H), 6.73 (d, J = 8 Hz,
3
1H), 7.09 (t, J = 8 Hz, 1H), 7.21 (d, J = 8 Hz, 1H), 7.37–
1
3
7.45 (m, 3H), 7.54 (br t, J = 8 Hz, 2H). C NMR
(100 MHz, CDCl /DMSO = 3:4 (v/v)): d 36.81, 107.81,
3
2
364; (d) Dehli, J. R.; Legros, J.; Bolm, C. Chem.
118.53, 124.97, 125.26, 126.58, 128.02, 129.39, 129.45,
134.27, 145.93, 172.31. HRMS (ES+): calcd for
Commun. 2005, 973–986; (e) Ley, S. V.; Thomas, A. W.
Angew. Chem., Int. Ed. 2003, 42, 5400–5449; (f) Kunz, K.;
Scholz, U.; Ganzer, D. Synlett 2003, 2428–2439.
C H11BrNO (M+H) 288.0024; found 288.0023. Com-
14
1
pound 10: H NMR (400 MHz, CDCl
3
): d 3.70 (s, 2H),
2
1. Kiyomori, A.; Marcoux, J. F.; Buchwald, S. L. Tetra-
hedron Lett. 1999, 40, 2657–2660.
2. (a) Lambers, M. M. H.; De Lange, B.; De Vries, A. H. M.;
De Vries, J. G.; Sereinig, N. PCT Int. Appl., to DSM, WO
6.94 (d, J = 8 Hz, 1H), 7.16 (t, J = 8 Hz, 1H), 7.28 (d,
1
3
J = 8 Hz, 1H), 7.47 (br s, 2H), 8.90 (br s, 2H). C NMR
(100 MHz, CDCl /DMSO = 3:4 (v/v)): d 37.15, 108.42,
119.10, 120.20, 125.57, 126.01, 129.59, 141.92, 144.10,
2
3