Li et al.
Concise Report
129.3, 127.3, 126.9, 117.5 (d, 3JC-F = 9.4 Hz), 117.2, 113.3 (d, 2JC-F
=
1H NMR (600 MHz, CDCl3) δ: 8.35 (d, J = 8.3 Hz, 1H), 7.66 (d, J =
7.4 Hz, 1H), 7.42—7.38 (m, 1H), 7.37—7.33 (m, 1H), 7.28 (dd, J =
11.2, 8.5 Hz, 4H), 7.06 (d, J = 8.1 Hz, 2H), 6.97 (d, J = 8.7 Hz, 2H),
3.90 (s, 3H), 2.30 (s, 3H), 2.06 (s, 3H). 13C NMR (151 MHz, CDCl3) δ:
160.2, 144.8, 142.8, 137.0, 135.3, 133.1, 131.3, 129.4, 126.9,
125.3, 124.3, 122.7, 119.8, 117.0, 116.3, 112.8, 55.3, 21.6, 18.3.
2
25.18 Hz), 105.5 (d, JC-F = 25.18 Hz), 21.6, 18.2. HRMS (ESI) m/z
calcd for C22H18FNNaO2S2+ [M + Na+] 434.0655, found 434.0656.
5-Chloro-3-(methylthio)-2-phenyl-1-tosyl-1H-indole (2d). Fol-
lowing the general procedure for preparation of products 2, com-
pound 2d was purified by silica gel chromatography (10% EtOAc/
o
1
+
PE). Yield: 190 mg, 89%, a white solid, m.p. 201—203 C. H NMR
(600 MHz, CDCl3) δ: 8.28 (d, J = 8.9 Hz, 1H), 7.64 (t, J = 8.6 Hz, 1H),
7.53—7.47 (m, 1H), 7.44 (t, J = 7.4 Hz, 2H), 7.34—7.37 (m, 3H),
HRMS (ESI) m/z calcd for C23H21NNaO3S2 [M + Na+] 446.0855,
found 446.0856.
4-Methyl-N-(2-(3-(methylthio)-1-tosyl-1H-indol-2-yl)phenyl)-
7.26 (d, J = 8.5 Hz, 3H), 7.08 (d, J = 8.4 Hz, 2H), 2.32 (s, 3H), 2.03 (s, benzenesulfonamide (2j). Following the general procedure for
3H). 13C NMR (151 MHz, CDCl3) δ: 145.1, 144.2, 135.3, 135.0,
132.6, 131.7, 130.3, 130.2, 129.5, 129.3, 127.3, 126.9, 125.7,
119.5, 117.3, 116.7, 21.6, 18.3. HRMS (ESI) m/z calcd for
C22H1835ClNNaO2S2+ [M + Na+] 450.0360, found 450.0364.
preparation of products 2, compound 2j was purified by silica gel
chromatography (10% EtOAc/PE). Yield: 270 mg, 96%, a white
o
1
solid, m.p. 174—175 C. H NMR (600 MHz, CDCl3) δ: 8.40 (d, J =
8.4 Hz, 1H), 7.70 (d, J = 8.1 Hz, 2H), 7.66 (d, J = 7.7 Hz, 1H),
7.53—7.47 (m, 2H), 7.41 (dd, J = 15.6, 7.9 Hz, 2H), 7.29 (d, J = 8.4
Hz, 2H), 7.17—7.08 (m, 5H), 6.96 (dd, J = 7.6, 1.3 Hz, 1H), 6.75 (d,
J = 7.3 Hz, 1H), 2.34 (d, J = 9.4 Hz, 6H), 1.97 (s, 3H). 13C NMR (101
MHz, CDCl3) δ: 145.6, 143.8, 137.2, 137.0, 136.9, 136.7, 134.6,
132.9, 130.9, 130.7, 129.7, 129.6, 127.2, 127.0, 126.3, 124.5,
123.3, 122.0, 120.1, 119.8, 119.7, 116.1, 77.4, 77.1, 76.8, 21.7,
5-Methyl-3-(methylthio)-2-phenyl-1-tosyl-1H-indole (2e). Fol-
lowing the general procedure for preparation of products 2,
compound 2e was purified by silica gel chromatography (3%
o
EtOAc/PE). Yield: 187 mg, 92%, a white solid, m.p. 119—121 C.
1H NMR (600 MHz, CDCl3) δ: 8.22 (dd, J = 8.5, 1.5 Hz, 1H),
7.50—7.40 (m, 4H), 7.39—7.34 (m, 2H), 7.28 (dd, J = 8.2, 1.2 Hz,
2H), 7.23 (d, J = 8.5 Hz, 1H), 7.06 (d, J = 8.3 Hz, 2H), 2.47 (s, 3H),
2.30 (s, 3H), 2.05 (d, J = 0.9 Hz, 3H). 13C NMR (151 MHz, CDCl3) δ:
144.7, 142.9, 135.2, 134.1, 131.8, 131.4, 130.8, 129.3, 129.0,
127.2, 126.9, 119.7, 117.2, 115.9, 21.5, 21.4, 18.3. HRMS (ESI) m/z
calcd for C23H21NNaO2S2+ [M + Na+] 430.0906 found 430.0909.
2-(3-Fluorophenyl)-3-(methylthio)-1-tosyl-1H-indole (2f). Fol-
lowing the general procedure for preparation of products 2,
compound 2f was purified by silica gel chromatography (5%
+
21.6, 18.1. HRMS (ESI) m/z calcd for C29H26N2NaO4S3 [M + Na+]
585.0947, found 585.0948.
2-(2-Bromo-5-(trifluoromethyl)phenyl)-3-(methylthio)-1-tosyl-
1H-indole (2k). Following the general procedure for preparation of
products 2, compound 2k was purified by silica gel chromatog-
raphy (3% EtOAc/PE). Yield: 115 mg, 43%, a white solid, m.p.
110—111 oC. 1H NMR (600 MHz, CDCl3) δ: 8.37 (dd, J = 8.4, 2.9 Hz,
1H), 7.84 (d, J = 8.4 Hz, 1H), 7.75 (d, J = 7.7 Hz, 1H), 7.60 (d, J = 8.4
Hz, 1H), 7.48 (t, J = 7.8 Hz, 1H), 7.41 (dd, J = 17.5, 8.0 Hz, 3H), 7.29
(s, 1H), 7.15 (d, J = 8.2 Hz, 2H), 2.34 (s, 3H), 2.17 (d, J = 2.2 Hz, 3H).
13C NMR (151 MHz, CDCl3) δ: 145.5, 138.8, 136.6, 135.8, 133.8,
o
1
EtOAc/PE). Yield: 113 mg, 55%, a white solid, m.p. 90—91 C. H
NMR (600 MHz, CDCl3) δ: 8.35 (dd, J = 8.4, 2.8 Hz, 1H), 7.74—7.66
(m, 1H), 7.48—7.35 (m, 3H), 7.31 (dd, J = 8.7, 2.0 Hz, 2H),
7.22—7.15 (m, 2H), 7.11—7.07 (m, 2H), 7.08—7.01 (m, 1H), 2.32
(s, 3H), 2.08 (d, J = 1.3 Hz, 3H). 13C NMR (151 MHz, CDCl3) δ: 161.7
3
133.05, 130.7, 130.3, 130.0 (q, JC-F = 3.8 Hz), 129.8, 128.9 (q,
2JC-F = 33.2 Hz), 127.2 (q, 3JC-F = 3.6 Hz), 126.9, 126.1, 124.2, 123.7
3
1
(d, 1JC-F = 246.3 Hz), 145.03, 141.13, 137.10, 135.11, 132.7 (d, JC-F
(q, JC-F = 272.2 Hz), 120.2, 118.0, 115.4, 21.5, 18.1. HRMS (ESI)
3
4
+
= 8.2 Hz), 131.01, 129.45, 128.7 (d, JC-F = 8.2 Hz), 127.7 (d, JC-F
=
m/z calcd for C23H1779BrF3NNaO2S2 [M + Na+] 561.9728, found
2
2.8 Hz), 126.83, 125.79, 124.41, 120.01, 118.7 (d, JC-F = 22.4 Hz),
118.08, 116.21, 116.0 (d, 2JC-F = 21.0 Hz), 21.52, 18.27. HRMS (ESI)
m/z calcd for C22H18FNNaO2S2+ [M + Na+] 434.0655, found 434.0651.
2-(4-Fluorophenyl)-3-(methylthio)-1-tosyl-1H-indole (2g). Fol-
lowing the general procedure for preparation of products 2,
compound 2g was purified by silica gel chromatography (5%
561.9729.
2-(2-Bromo-5-chlorophenyl)-3-(methylthio)-1-tosyl-1H-indole
(2l). Following the general procedure for preparation of products
2, compound 2l was purified by silica gel chromatography (5%
o
EtOAc/PE). Yield: 91 mg, 36%, a white solid, m.p. 144—146 C. 1H
NMR (600 MHz, CDCl3) δ: 8.34 (d, J = 8.4 Hz, 1H), 7.74 (d, J = 7.6
Hz, 1H), 7.62 (d, J = 8.6 Hz, 1H), 7.49—7.45 (m, 3H), 7.41—7.36 (m,
1H), 7.33 (dd, J = 8.6, 2.5 Hz, 1H), 7.18 (d, J = 8.1 Hz, 2H), 7.05 (d,
J = 2.5 Hz, 1H), 2.35 (s, 3H), 2.18 (s, 3H). 13C NMR (151 MHz,
CDCl3) δ: 145.3, 139.0, 136.5, 135.8, 134.2, 133.4, 133.1, 132.3,
130.7, 130.2, 129.7, 127.1, 126.0, 124.5, 124.1, 120.1, 117.6,
o
EtOAc/PE). Yield: 183 mg, 89%, a white solid, m.p. 123—125 C.
1H NMR (400 MHz, CDCl3) δ: 8.36 (d, J = 8.3 Hz, 1H), 7.68 (dd, J =
7.7, 0.7 Hz, 1H), 7.43 (ddd, J = 8.4, 7.3, 1.4 Hz, 1H), 7.40—7.31 (m,
3H), 7.27 (d, J = 8.4 Hz, 2H), 7.14 (ddd, J = 8.7, 5.8, 2.5 Hz, 2H),
7.07 (d, J = 8.1 Hz, 2H), 2.31 (s, 3H), 2.06 (s, 3H). 13C NMR (101
1
+
MHz, CDCl3) δ: 163.2 (d, JC-F = 250.4 Hz), 145.0, 141.6, 137.0,
115.3, 21.6, 18.1. HRMS (ESI) m/z calcd for C22H1779BrClNNaO2S2
135.1, 133.6 (d, 3JC-F = 8.5 Hz), 131.0, 129.5, 126.8, 126.5 (d, 4JC-F
=
[M + Na+] 527.9465, found 527.9467.
3.5 Hz), 125.7, 124.4, 119.9, 117.7, 116.2, 114.5 (d, 2JC-F = 21.8 Hz),
3-(Methylthio)-2-(naphthalen-1-yl)-1-tosyl-1H-indole
(2m).
+
21.6, 18.3. HRMS (ESI) m/z calcd for C22H18FNNaO2S2 [M + Na+]
Following the general procedure for preparation of products 2,
compound 2m was purified by silica gel chromatography (10%
434.0655, found 434.0660.
o
2-(4-Bromophenyl)-3-(methylthio)-1-tosyl-1H-indole
(2h).
EtOAc/PE). Yield: 205 mg, 93%, a white solid, m.p. 142—143 C.
Following the general procedure for preparation of products 2,
compound 2h was as purified by silica gel chromatography (5%
1H NMR (600 MHz, CDCl3) δ: 8.45 (d, J = 8.4 Hz, 1H), 7.98 (d, J =
8.2 Hz, 1H), 7.87 (d, J = 8.2 Hz, 1H), 7.78 (d, J = 7.7 Hz, 1H), 7.55 (t,
J = 7.6 Hz, 1H), 7.48 (dd, J = 8.3, 7.3 Hz, 1H), 7.42 (q, J = 7.6 Hz, 2H),
7.38 (d, J = 7.0 Hz, 1H), 7.27 (d, J = 8.4 Hz, 1H), 7.24—7.19 (m, 3H),
6.92 (d, J = 8.2 Hz, 2H), 2.24 (s, 3H), 2.00 (s, 3H). 13C NMR (101
MHz, CDCl3) δ: 144.8, 140.2, 136.9, 135.4, 133.5, 133.0, 130.6,
130.4, 129.9, 129.3, 128.4, 128.2, 127.0, 126.2, 125.8, 125.7,
o
EtOAc/PE). Yield: 155 mg, 66%, a white solid, m.p. 146—147 C.
1H NMR (600 MHz, CDCl3) δ: 8.35 (d, J = 8.4 Hz, 1H), 7.67 (d, J =
7.7 Hz, 1H), 7.57 (d, J = 8.2 Hz, 2H), 7.42 (t, J = 7.8 Hz, 1H), 7.36 (t,
J = 7.5 Hz, 1H), 7.26 (dt, J = 11.1, 5.5 Hz, 4H), 7.07 (d, J = 8.1 Hz,
2H), 2.30 (s, 3H), 2.06 (s, 3H). 13C NMR (151 MHz, CDCl3) δ: 145.1,
141.4, 137.2, 135.0, 133.3, 131.1, 130.6, 129.6, 129.5, 126.8,
125.8, 124.5, 123.6, 120.0, 118.1, 116.3, 21.6, 18.3. HRMS (ESI)
125.5, 124.4, 124.0, 119.8, 117.7, 115.6, 21.5, 18.4. HRMS (ESI)
+
m/z calcd for C26H21NNaO2S2 [M
466.0906.
+
Na+] 466.0906, found
+
m/z calcd for C22H1879BrNNaO2S2 [M + Na+] 493.9855, found
493.9855.
3-(Methylthio)-2-(thiophen-2-yl)-1-tosyl-1H-indole (2n). Fol-
lowing the general procedure for preparation of products 2,
compound 2n was purified by silica gel chromatography (5%
EtOAc/PE). Yield: 183 mg, 92%, a white solid, m.p. 80—81 C. H
NMR (600 MHz, CDCl3) δ: 8.35 (d, J = 8.4 Hz, 1H), 7.72—7.66 (m,
2-(4-Methoxyphenyl)-3-(methylthio)-1-tosyl-1H-indole
Following the general procedure for preparation of products 2,
compound 2i was as purified by silica gel chromatography (10%
(2i).
o
1
o
EtOAc/PE). Yield: 181 mg, 86%, a white solid, m.p. 147—148 C.
1218
© 2021 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
Chin. J. Chem. 2021, 39, 1211-1224