Beilstein J. Org. Chem. 2019, 15, 1162–1171.
zenethiol (14m). The residue was purified on silica gel (from provincial Fonds de Recherche du Québec, Nature et Technolo-
100% Hex to 20% EtOAc/Hex) to afford 1m (57.4 mg, 80%) gies (FRQNT) team grant and by the Centre in Green Chem-
and 26m (1.1 mg, 2%) as yellow oils. 1m: Spectral data was istry and Catalysis (CGCC).
identical to literature compound [38]. 1H NMR (300 MHz,
ORCID® iDs
CDCl3) δ 7.34 (d, J = 9.0 Hz, 2H), 6.86 (d, J = 8.7 Hz, 2H),
3.80 (s, 3H), 2.22–2.14 (m, 1H), 1.01–0.95 (m, 2H), 0.70–0.65
(m, 2H). 26m: Spectral data was identical to literature com-
References
1. Fyfe, M. C. T.; White, J. R.; Taylor, A.; Chatfield, R.; Wargent, E.;
pound [61]. 1H NMR (300 MHz, CDCl3) δ 7.40 (d, J = 9.0 Hz,
4H), 6.83 (d, J = 8.7 Hz, 4H), 3.80 (s, 6H).
Printz, R. L.; Sulpice, T.; McCormack, J. G.; Procter, M. J.; Reynet, C.;
Widdowson, P. S.; Wong-Kai-In, P. Diabetologia 2007, 50, 1277–1287.
(3-Bromophenyl)(cyclopropyl)sulfane (1n) and 1,2-bis(3-
bromophenyl)disulfane (26n). The general procedure was fol-
2. Mao, W.; Ning, M.; Liu, Z.; Zhu, Q.; Leng, Y.; Zhang, A.
lowed on 0.484 mmol scale starting from 3-bromobenzenethiol
(14n). The residue was purified on silica gel (100% Hex) to
afford 1n (49.9 mg, 45%) and 26n (5.5 mg, 6%) as a colorless
and a yellow oil, respectively. 1n: Spectral data was identical to
literature compound [38]. 1H NMR (300 MHz, CDCl3) δ
7.51–7.50 (t, J = 0.9 Hz, 1H), 7.27–7.24 (m, 2H), 7.13 (t,
J = 3.9 Hz, 1H), 2.19–2.15 (m, 1H), 1.12–1.09 (m, 2H),
0.72–0.69 (m, 2H). 26n: Spectral data was identical to litera-
ture compound [38]. 1H NMR (300 MHz, CDCl3) δ 7.64–7.62
(m, 2H), 7.42–7.35 (m, 4H), 7.18 (t, J = 7.8 Hz, 2H).
Bioorg. Med. Chem. 2012, 20, 2982–2991.
3. ClinicalTrialsgov identifier: NCT01247363: A Study of LY2608204 in
Patients with Type 2 Diabetes.
4. Deshpande, A. M.; Bhuniya, D.; De, S.; Dave, B.; Vyavahare, V. P.;
Kurhade, S. H.; Kandalkar, S. R.; Naik, K. P.; Kobal, B. S.;
Kaduskar, R. D.; Basu, S.; Jain, V.; Patil, P.; Chaturvedi Joshi, S.;
Bhat, G.; Raje, A. A.; Reddy, S.; Gundu, J.; Madgula, V.; Tambe, S.;
Shitole, P.; Umrani, D.; Chugh, A.; Palle, V. P.; Mookhtiar, K. A.
Eur. J. Med. Chem. 2017, 133, 268–286.
5. ClinicalTrials.gov identifier: NCT01247363: Phase 1 study of
LY2608204 in patients with Type 2 Diabetes Melitus.
6. Lücking, U.; Jautelat, R.; Krüger, M.; Brumby, T.; Lienau, P.;
Schäfer, M.; Briem, H.; Schulze, J.; Hillisch, A.; Reichel, A.;
Wengner, A. M.; Siemeister, G. ChemMedChem 2013, 8, 1067–1085.
Methyl 2-(cyclopropylthio)benzoate (1o) and dimethyl 2,2'-
disulfanediyldibenzoate (26o). The general procedure was fol-
lowed on 0.400 mmol scale starting from methyl 2-mercapto-
benzoate (14o). The residue was purified on silica gel (from
100% Hex to 20% EtOAC/Hex) to afford 1o (36.7 mg, 44%)
and 26o (24.1 mg, 36%) as a yellow oil and a white solid, re-
spectively. 1o: Spectral data was identical to literature com-
pound [38]. 1H NMR (300 MHz, CDCl3) δ 7.99 (dd, J = 8.0,
1.7 Hz, 1H), 7.79 (dd, J = 8.1, 1.2 Hz, 1H), 7.47 (ddd, J = 8.7,
7.2, 1.5 Hz, 1H), 7.15 (ddd, J = 9.0, 7.2, 1.2 Hz, 1H), 3.89 (s,
3H), 2.12–2.04 (m, 1H), 1.17–1.10 (m, 2H), 0.74–0.69 (m, 2H).
26o: mp 133.0–135.5 °C. Spectral data was identical to litera-
ture compound [62]. 1H NMR (300 MHz, CDCl3) δ 8.06 (dd,
J = 7.8, 1.5 Hz, 2H), 7.76 (dd, J = 8.3, 1.1 Hz, 2H), 7.41 (ddd,
J = 8.3, 7.3, 1.3 Hz, 2H), 7.23 (dd, J = 7.5, 1.2, 2H), 3.99 (s,
6H).
7. Nishimura, N.; Norman, M. H.; Liu, L.; Yang, K. C.; Ashton, K. S.;
Bartberger, M. D.; Chmait, S.; Chen, J.; Cupples, R.; Fotsch, C.;
Helmering, J.; Jordan, S. R.; Kunz, R. K.; Pennington, L. D.;
Poon, S. F.; Siegmund, A.; Sivits, G.; Lloyd, D. J.; Hale, C.;
Jean, D. J. St. J. Med. Chem. 2014, 57, 3094–3116.
8. Lohier, J.-F.; Glachet, T.; Marzag, H.; Gaumont, A.-C.; Reboul, V.
9. Reck, M.; Horn, L.; Novello, S.; Barlesi, F.; Albert, I.; Juhász, E.;
Kowalski, D.; Robinet, G.; Cadranel, J.; Bidoli, P.; Chung, J.;
Fritsch, A.; Drews, U.; Wagner, A.; Govindan, R. J. Thorac. Oncol.
10.Bumgardner, C. L.; Lever, J. R.; Purrington, S. T. Tetrahedron Lett.
11.Trost, B. M.; Vladuchick, W. C. Synthesis 1978, 821.
12.Kwon, T. W.; Smith, M. B. Synth. Commun. 1992, 22, 2273–2285.
Supporting Information
13.Trost, B. M.; Keeley, D. E.; Arndt, H. C.; Bogdanowicz, M. J.
14.Horiguchi, Y.; Suehiro, I.; Sasaki, A.; Kuwajima, I. Tetrahedron Lett.
15.Grover, H. K.; Emmett, M. R.; Kerr, M. A. Org. Biomol. Chem. 2015, 13,
Supporting Information File 1
Copies of NMR spectra of synthesized compounds.
16.Bernard, A. M.; Frongia, A.; Secci, F.; Delogu, G.; Ollivier, J.;
Piras, P. P.; Salaün, J. Tetrahedron 2003, 59, 9433–9440.
Acknowledgements
This work was supported by Boehringer Ingelheim Pharmaceu-
ticals, Inc. through a Scientific Advancement Grant, by a
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