H
H. P. Mangunuru et al.
Paper
Synthesis
HRMS (ESI): m/z [M + H]+ calcd for C23H22NO3: 360.1600; found:
360.1592.
References
(1) Current address: Department of Chemical and Life Science
Engineering, Virginia Commonwealth University, 737 N. 5th St.,
Richmond, VA 23219, USA.
(2) Current address: Department of Chemistry, University of Michi-
gan, Ann Arbor, MI 48109, USA.
(3) (a) Cao, Z.-Y.; Wang, Y.-H.; Zeng, X.-P.; Zhou, J. Tetrahedron Lett.
2014, 55, 2571. (b) Shen, K.; Liu, X.; Lin, L.; Feng, X. Chem. Sci.
2012, 3, 327. (c) Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal.
2010, 352, 1381. (d) Galliford, C. V.; Scheidt, K. A. Angew. Chem.
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(4) Richmond, E.; Ling, K. B.; Duguet, N.; Manton, L. B.; Celebi-
Olcum, N.; Lam, Y.-H.; Alsancak, S.; Slawin, A. M. Z.; Houk, K. N.;
Smith, A. D. Org. Biomol. Chem. 2015, 13, 1807.
3-Methyl-1,3-diphenylindolin-2-one (40)
Prepared following the general arylation procedure and isolated as a
yellow solid in 63% yield; 74% ee; mp 135–137 °C.
1H NMR (400 MHz, CDCl3): δ = 7.53–7.48 (m, 2 H), 7.45–7.43 (m, 1 H),
7.42–7.36 (m, 4 H), 7.35–7.29 (m, 2 H), 7.28–7.21 (m, 3 H), 7.11 (dt, J =
7.6, 1.0 Hz, 1 H), 6.92–6.89 (m, 1 H), 1.90 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 178.9, 143.3, 141.1, 134.9, 134.8,
129.7, 128.8, 128.1, 127.5, 126.9, 126.8, 124.7, 123.4, 109.9, 52.6, 24.2.
Chiral SFC conditions: Lux Cellulose1, 4.6 × 150 mm, particle size: 3
μm, temperature: 30 °C, A: CO2, B: MeOH, isocratic: A/B: 50:50, v/v,
flow rate: 3.0 mL/min, tmajor = 4.60 min, tminor = 4.42 min.
HRMS (ESI): m/z [M + H]+ calcd for C21H18NO: 300.1388; found:
(5) Natarajan, A.; Guo, Y.; Harbinski, F.; Fan, Y.-H.; Chen, H.; Luus,
L.; Diercks, J.; Aktas, H.; Chorev, M.; Halperin, J. A. J. Med. Chem.
2004, 47, 4979.
300.1382.
4-(3-Methyl-2-oxo-1-phenylindolin-3-yl)benzonitrile (41)
(6) Hewawasam, P.; Gribkoff, V. K.; Pendri, Y.; Dworetzky, S. I.;
Meanwell, N. A.; Martinez, E.; Boissard, C. G.; Post-Munson, D.
J.; Trojnacki, J. T.; Yeleswaram, K.; Pajor, L. M.; Knipe, J.; Gao, Q.;
Perrone, R.; Starrett, J. E. Bioorg. Med. Chem. Lett. 2002, 12, 1023.
(7) Lim, J. W.; Kim, K. H.; Moon, H. R.; Kim, J. N. Tetrahedron Lett.
2016, 57, 784.
Prepared following the general arylation procedure and isolated as a
yellow solid in 59% yield; 70% ee; mp 133–135 °C.
1H NMR (400 MHz, CDCl3): δ = 7.63–7.60 (m, 2 H), 7.54–7.50 (m, 4 H),
7.43–7.39 (m, 3 H), 7.28 (t, J = 7.7 Hz, 1 H), 7.23 (m, 1 H), 7.16 (t, J = 7.5
Hz, 1 H), 6.93 (d, J = 7.7 Hz, 1 H), 1.91 (s, 3 H).
(8) For recent publications, see: (a) Mai, C.-K.; Sammons, M. F.;
Sammakia, T. Org. Lett. 2010, 12, 2306. (b) Li, P.; Buchwald, S. L.
Angew. Chem. Int. Ed. 2011, 50, 6396. (c) Pietruszka, J.; Wang, C.
ChemCatChem 2012, 4, 782. (d) Xiao, Z. K.; Yin, H. Y.; Shao, L.-X.
Org. Lett. 2013, 15, 1254. (e) Jin, Y.; Chen, M.; Ge, S.; Hartwig, J.
F. Org. Lett. 2017, 19, 1390. (f) Moghaddam, F. M.; Tavakoli, G.;
Latifi, F.; Saeednia, B. Catal. Commun. 2016, 75, 37. (g) Zhai, C.;
Xing, D.; Jing, C.; Zhou, J.; Wang, C.; Wang, D.; Hu, W. Org. Lett.
2014, 16, 2934. (h) Duan, J.; Kwong, F. Y. J. Org. Chem. 2017, 82,
6468. (i) Yu, J.-S.; Zhou, F.; Liu, Y.-L.; Zhou, J. Synlett 2015, 26,
2491. (j) Kaur, J.; Chimni, S. S.; Mahajan, S.; Kumar, A. RSC Adv.
2015, 5, 52481. (k) Zhou, L.-J.; Zhang, Y.-C.; Jiang, F.; He, G.; Yan,
J.; Lu, H.; Zhang, S.; Shi, F. Adv. Synth. Catal. 2016, 358, 3069.
(l) Guo, W.; Liu, Y.; Li, C. Org. Lett. 2017, 19, 1044. (m) Jiang, F.;
Zhao, D.; Yang, X.; Yuan, F.-R.; Mei, G.-J.; Shi, F. ACS Catal. 2017,
7, 6984.
13C NMR (100 MHz, CDCl3): δ = 177.8, 146.4, 143.3, 134.4, 133.4,
132.6, 129.9, 128.8, 128.5, 127.9, 126.9, 126.7, 124.7, 123.8, 118.9,
111.6, 110.2, 52.6, 24.4.
Chiral SFC conditions: ES-CCC, 4.6 × 150 mm, particle size: 3 μm, tem-
perature: 30 °C, A: CO2, B: MeOH, isocratic: A/B: 50:50, v/v, flow rate:
3.0 mL/min, tmajor = 5.40 min, tminor = 5.11 min.
HRMS (ESI): m/z [M + H]+ calcd for C22H17N2O: 325.1341; found:
325.1335.
Methyl 4-(3-Methyl-2-oxo-1-phenylindolin-3-yl)benzoate (42)
Prepared following the general arylation procedure and isolated as a
brown liquid in 55% yield; 66% ee.
1H NMR (400 MHz, CDCl3): δ = 7.99 (m, 2 H), 7.54–7.49 (m, 2 H), 7.49–
7.45 (m, 2 H), 7.44–7.38 (m, 3 H), 7.29–7.26 (m, 1 H), 7.25–7.21 (m, 1
H), 7.14 (dt, J = 7.5, 1.0 Hz, 1 H), 6.92–6.89 (m, 1 H), 3.90 (s, 3 H), 1.93
(s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 178.3, 166.9, 146.1, 143.3, 134.6,
134.2, 130.0, 129.8, 129.4, 128.5, 128.3, 127.0, 126.8, 124.7, 123.6,
110.0, 52.6, 52.3, 24.2.
(9) (a) Durbin, M. J.; Willis, M. C. Org. Lett. 2008, 10, 1413.
(b) Altman, R. A.; Hyde, A. M.; Huang, X.; Buchwald, S. L. J. Am.
Chem. Soc. 2008, 130, 9613. (c) Taylor, A. M.; Altman, R. A.;
Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 9900.
(10) (a) Tang, W.; Qu, B.; Capacci, A. G.; Rodriguez, S.; Wei, X.;
Haddad, N.; Narayanan, B.; Ma, S.; Grinberg, N.; Yee, N. K.;
Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2010, 12, 176.
(b) Tang, W.; Capacci, A. G.; Wei, X.; Li, W.; White, A.; Patel, N.
D.; Savoie, J.; Gao, J.; Rodriguez, S.; Qu, B.; Haddad, N.; Lu, B. Z.;
Krishnamurthy, D.; Yee, N. K.; Senanayake, C. H. Angew. Chem.
Int. Ed. 2010, 49, 5879. (c) Tang, W.; Patel, N. D.; Xu, G.; Xu, X.;
Savoie, J.; Ma, S.; Hao, M.-H.; Keshipeddy, S.; Capacci, A. G.; Wei,
X.; Zhang, Y.; Gao, J.; Li, W.; Rodriguez, S.; Lu, B. Z.; Yee, N. K.;
Senanayake, C. H. Org. Lett. 2012, 14, 2258.
Chiral SFC conditions: Lux Cellulose 2, 4.6 × 150 mm, particle size: 3
μm, temperature: 30 °C, A: CO2, B: MeOH, isocratic: A/B: 50:50, v/v,
flow rate: 3.0 mL/min, tmajor = 6.04 min, tminor = 5.44 min.
HRMS (ESI): m/z [M + H]+ calcd for C23H20NO3: 358.1443; found:
358.1436.
Supporting Information
(11) For selected publications, see: (a) Wei, X.; Qu, B.; Zeng, X.;
Savoie, J.; Fandrick, K. R.; Desrosiers, J.-N.; Tcyrulnikov, S.;
Marsini, M. A.; Buono, F. G.; Li, Z.; Yang, B.-S.; Tang, W.; Haddad,
N.; Gutierrez, O.; Wang, J.; Lee, H.; Ma, S.; Campbell, S.; Lorenz,
J. C.; Eckhardt, M.; Himmelsbach, F.; Peters, S.; Patel, N. D.; Tan,
Z.; Yee, N. K.; Song, J. J.; Roschangar, F.; Kozlowski, M. C.;
Senanayake, C. H. J. Am. Chem. Soc. 2016, 138, 15473.
(b) Haddad, N.; Mangunuru, H. P. R.; Fandrick, K. R.; Qu, B.;
Supporting information for this article is available online at
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–I