1-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione → 1-Methyl-5-(2-(pyridin-3-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@H:15]3[CH2:19][O:20][C:21]3[CH:26]=C[CH:24]=[CH:23][CH:22]=3)(=[O:13])=[O:12])=[CH:8][CH:9]=2)[C:4](=[O:27])[C:3]1=[O:28].[N:29]1C=CC=C(OCC2CCCN2S(C2C=C3C(=CC=2)NC(=O)C3=O)(=O)=O)C=1>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[CH2:19][O:20][C:21]3[CH:26]=[N:29][CH:24]=[CH:23][CH:22]=3)(=[O:12])=[O:13])=[CH:8][CH:9]=2)[C:4](=[O:27])[C:3]1=[O:28]Participants
3
Procedure
1-Methyl-5-(2-(pyridin-3-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (21a) was prepared according to the same procedure for compound 11a, except using compound 20, and the crude product was purified with ethyl acetate to afford 55 mg (55%) of 21a as a yellow solid, mp 142.1-143.4° C. 1H NMR (300 MHz, CDCl3) δ 8.24 (d, J=2.7, 1H), 8.22 (dd, J=3.9 Hz, J=2.1 Hz, 1H), 8.08 (dd, J=8.4, J=2.1 Hz, 1H), 7.26 (s, 1H), 7.21 (m, 2H), 7.00 (d, J=8.4 Hz, 1H), 4.22 (m, 1H), 3.98 (m, 2H), 3.53 (m, 1H), 3.30 (s, 3H), 3.22 (m, 2H), 2.03 (m, 2H), 1.80 (m, 2H). LCMS m/e: 401.84 (M+H). Anal. Calcd for C19H19N3O5S: C, 56.85, H, 4.77; N, 10.47. Found: C, 56.48, H, 4.87; N, 10.19.
Workup
- custom1-Methyl-5-(2-(pyridin-3-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (21a) was prepared
- customthe crude product was purified with ethyl acetate
Sources & evidence
- ORD record
- ord-1b9717bd302b4451b5c95da0c9c7484a
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329686B2
Reaction notes
Loading…