N,N-Dimethylindoline-5-Sulfonamide → 1-{[3-Chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetyl}-N,N-dimethylindoline-5-sulfonamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([O:13][C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16]([Cl:22])[CH:15]=2)[CH:12]=1)[O:5][CH2:6][C:7](Cl)=[O:8].[CH3:23][N:24]([CH3:37])[S:25]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH2:32][CH2:31]2)(=[O:27])=[O:26]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([O:13][C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16]([Cl:22])[CH:15]=2)[CH:12]=1)[O:5][CH2:6][C:7]([N:33]1[C:34]2[C:30](=[CH:29][C:28]([S:25]([N:24]([CH3:37])[CH3:23])(=[O:26])=[O:27])=[CH:36][CH:35]=2)[CH2:31][CH2:32]1)=[O:8]Participants
4
Procedure
41 mg (0.115 mmol) of [3-chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetyl chloride (5-4) and 26 mg (0.115 mmol) of N,N-dimethylindoline-5-sulfonamide (23-1) were refluxed in benzene. When the reaction was complete the benzene was evaporated off and the residue was purified on a silica column eluted with EtOAc:hexanes (3:97 to 1:1). Recovered the desired compound 23-2. HRMS: measured 546.0665; theoretical 546.0652. 1H NMR (CDCl3): 2.70 (s, 6H), 3.35 (t, 2H), 4.23 (t, 2H), 4.78 (bs, 2H), 6.59 (t, 1H), 6.68 (t, 1H), 6.83 (m, 1H), 7.15 (m, 1H), 7.24 (m, 1H), 7.39 (m, 1H), 7.63 (bs, 1H), 7.66 (bd, 1H), 8.34 (bd, 1H).
Workup
- customwas evaporated off
- customthe residue was purified on a silica column
- washeluted with EtOAc:hexanes (3:97 to 1:1)
- customRecovered the desired compound 23-2
Sources & evidence
- ORD record
- ord-6bec5ebd92ce40729d07358fd348d051
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807684B2
Reaction notes
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