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Medicinal Chemistry Research (2021) 30:1588–1602
7.90 (dd, J = 8.3, 2.0 Hz, 1H), 7.75 (d, J = 1.9 Hz, 1H), 7.51
(d, J = 8.6 Hz, 2H), 7.26–7.23 (m, 1H), 6.84 (d, J = 8.6 Hz,
2H), 4.54 (s, 2H). 13C NMR (101 MHz, DMSO-d6) δ 183.45,
169.34, 158.79, 157.80, 149.53, 136.45, 136.23, 129.70,
128.00 (2C), 122.10, 118.24, 116.26 (2C), 112.02, 41.79 ppm.
HRMS (ESI) m/z calcd for [M-H]− 296.06, found 296.0566.
6h as red powder (112 mg, 68%). M.p. 218–220 °C; purity:
99.83%, H NMR (400 MHz, DMSO-d6) δ 13.20 (s, 1H),
1
8.12 (dd, J = 8.3, 1.9 Hz, 1H), 7.99 (d, J = 1.7 Hz, 1H), 7.91
(d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.1 Hz, 2H), 7.39 (d, J =
8.3 Hz, 1H), 7.14 (t, J = 55.9 Hz, 1H), 4.62 (s, 2H). 13C NMR
(101 MHz, DMSO-d6) δ 183.19, 169.30, 158.79, 150.79,
141.41, 137.24, 135.10, 127.30(2C), 126.83 (t, J = 5.9 Hz),
123.18, 118.39, 117.67, 115.33, 112.98, 112.23, 41.87 ppm.
HRMS (ESI) m/z calcd for [M-H]− 330.07, found 330.0589.
2-(5-(3-hydroxyphenyl)-2,3-dioxoindolin-1-yl)acetic acid (6e)
The reaction was carried out according to the general proce-
dure F using compound 5e (171.5 mg, 0.5 mmol), con-
centrated HCl (2 mL) and THF (8 mL) to give 6e as red
powder (108 mg, 73%). M.p. 238–240 °C; purity: 99.94%, 1H
NMR (400 MHz, DMSO-d6) δ 13.22 (s, 1H), 9.57 (s, 1H),
7.94 (dd, J = 8.3, 1.9 Hz, 1H), 7.76 (d, J = 1.7 Hz, 1H),
7.29–7.24 (m, 2H), 7.09 (d, J = 7.8 Hz, 1H), 7.02 (d, J =
2-(2,3-dioxo-5-(p-tolyl)indolin-1-yl)acetic acid (6i) The reac-
tion was carried out according to the general procedure F
using compound 5i (169.5 mg, 0.5 mmol), concentrated HCl
(2 mL) and THF (8 mL) to give 6i as red powder (101 mg,
69%). M.p. 210–212 °C; purity: 99.84%, 1H NMR
(400 MHz, DMSO-d6) δ 13.26 (s, 1H), 7.98 (dd, J = 8.3,
1.9 Hz, 1H), 7.83 (d, J = 1.8 Hz, 1H), 7.59 (d, J = 8.1 Hz,
2H), 7.28 (dd, J = 8.1, 3.2 Hz, 3H), 4.56 (s, 2H), 2.35 (s, 3H).
13C NMR (101 MHz, DMSO-d6) δ 183.34, 169.32, 158.79,
150.12, 137.52, 136.73, 136.12 (d, J = 12.6 Hz,2C), 130.08
(2C), 126.68 (2C), 122.60, 118.29, 112.10, 41.82, 21.12 ppm.
HRMS (ESI) m/z calcd for [M-H]− 294.08, found 294.0772.
1.8 Hz, 1H), 6.79 (dd, J = 8.0, 1.8 Hz, 1H), 4.55 (s, 2H). 13
C
NMR (101 MHz, DMSO-d6) δ 183.29, 169.3, 158.79, 158.37,
150.31, 140.37, 136.93, 136.37, 130.55, 122.70, 118.25,
117.62, 115.17, 113.62, 112.10, 41.83 ppm. HRMS (ESI) m/z
calcd for [M-H]− 296.06, found 296.0575.
2-(2,3-dioxo-5-(3-(trifluoromethyl)phenyl)indolin-1-yl)acetic
acid (6f) The reaction was carried out according to the
general procedure F using compound 5f (196.5 mg,
0.5 mmol), concentrated HCl (2 mL) and THF (8 mL) to
give 6f as red powder (115 mg, 66%). M.p. 172–174 °C;
purity: 99.47%, 1H NMR (400 MHz, DMSO-d6) δ 13.26 (s,
1H), 8.11 (dd, J = 8.3, 2.0 Hz, 1H), 8.02 (dd, J = 10.9,
5.4 Hz, 3H), 7.74–7.69 (m, 2H), 7.34 (d, J = 8.3 Hz, 1H),
4.57 (s, 2H). 13C NMR (101 MHz, DMSO-d6) δ 183.14,
169.30, 158.79, 150.90, 140.03, 137.41, 134.51, 131.01,
130.72–130.14 (2C), 130.17, 126.01, 124.64, 123.48,
118.38, 112.23, 41.87 ppm. HRMS (ESI) m/z calcd for [M-
H]− 348.06, found 348.0507.
2-(5-(4-methoxyphenyl)-2,3-dioxoindolin-1-yl)acetic acid (6j)
The reaction was carried out according to the general proce-
dure F using compound 5j (177.5 mg, 0.5 mmol), concentrated
HCl (2 mL) and THF (8 mL) to give 6j as red powder
1
(105 mg, 68%). M.p. 192–194 °C; purity: 99.74%, H NMR
(400 MHz, DMSO-d6) δ 13.27 (s, 1H), 7.95 (dd, J = 8.3,
2.0 Hz, 1H), 7.81 (d, J = 1.8 Hz, 1H), 7.65–7.62 (m, 2H), 7.27
(d, J = 8.3 Hz, 1H), 7.04–7.00 (m, 2H), 4.55 (s, 2H), 3.80 (s,
3H). 13C NMR (101 MHz, DMSO-d6) δ 183.41, 169.33,
159.54, 158.79, 149.80, 136.47, 136.01, 131.31, 128.03(2 C),
122.35, 118.28, 114.91(2C), 112.08, 55.69, 41.81 ppm.
HRMS (ESI) m/z calcd for [M-H]− 310.08, found 310.0712.
2-(2,3-dioxo-5-(4-(trifluoromethyl)phenyl)indolin-1-yl)acetic
acid (6g) The reaction was carried out according to the
general procedure F using compound 5g (196.5 mg,
0.5 mmol), concentrated HCl (2 mL) and THF (8 mL) to
give 6g as red powder (110 mg, 65%). M.p. 202–204 °C;
purity: 99.49%, 1H NMR (400 MHz, DMSO-d6) δ 13.30 (s,
1H), 8.10 (dd, J = 8.3, 1.9 Hz, 1H), 7.97 (dd, J = 10.4,
5.0 Hz, 3H), 7.82 (d, J = 8.2 Hz, 2H), 7.36 (d, J = 8.3 Hz,
1H), 4.58 (s, 2H). 13C NMR (101 MHz, DMSO-d6) δ
183.10, 169.29, 158.79, 151.06, 142.94, 137.40, 134.46,
128.58, 128.26, 127.68 (2C), 126.27 (d, 2C), 123.37,
118.42, 112.29, 41.87 ppm. HRMS (ESI) m/z calcd for [M-
H]− 348.06, found 348.0496.
2-(5-(2,4-dimethoxyphenyl)-2,3-dioxoindolin-1-yl)acetic
acid (6k) The reaction was carried out according to the
general procedure F using compound 5k (192.5 mg,
0.5 mmol), concentrated HCl (2 mL) and THF (8 mL) to
give 6k as red powder (114 mg, 67%). M.p. 210–212 °C;
1
purity: 98.18% H NMR (400 MHz, DMSO-d6) δ 13.28 (s,
1H), 7.73 (dd, J = 8.2, 1.8 Hz, 1H), 7.61 (d, J = 1.6 Hz,
1H), 7.26 (d, J = 8.4 Hz, 1H), 7.21 (d, J = 8.3 Hz, 1H), 6.68
(d, J = 2.3 Hz, 1H), 6.63 (dd, J = 8.4, 2.3 Hz, 1H), 4.54 (s,
2H), 3.81 (s, 3H), 3.79 (s, 3H). 13C NMR (101 MHz,
DMSO-d6) δ 183.43, 169.36, 160.87, 158.81, 157.52,
149.47, 139.41, 133.92, 131.05, 125.32, 121.05, 117.54,
111.34, 105.92, 99.42, 56.10, 55.80, 41.74 ppm. HRMS
(ESI) m/z calcd for [M-H]− 340.09, found 340.0842.
2-(5-(4-(difluoromethyl)phenyl)-2,3-dioxoindolin-1-yl)acetic
acid (6h) The reaction was carried out according to the
general procedure
F
using compound 5h (187.5 mg,
2-(5-(3,4-dimethoxyphenyl)-2,3-dioxoindolin-1-yl)acetic
0.5 mmol), concentrated HCl (2 mL) and THF (8 mL) to give
acid (6l) The reaction was carried out according to the