4-Toluenesulfonyl chloride → HCID 22663271, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:22])[C:7]=1[NH:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:20]=[O:21])=[CH:16][NH:17]2)=[CH:13][CH:12]=1)=[O:10].[H-].[Na+].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>CN(C)C=O>[Cl:22][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:20]=[O:21])=[CH:16][N:17]2[S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])=[CH:13][CH:12]=1)=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
A stirred solution of N-(3,5-dichloro-pyridin-4-yl)-3-formyl-1H-indole-6-carboxamide (0.518 g, Example 18) in dimethylformamide at 0° C. was treated with sodium hydride (0.136 g). The mixture was stirred for 15 minutes, then cooled to −40° C. and then treated with 4-toluenesulphonyl chloride (0.325 g). The reaction mixture was gradually allowed to warm to −20° C. over a period of 90 minutes, then quenched with water (20 ml), then extracted three times with ethyl acetate (25 ml). The combined extracts were dried over sodium sulphate then evaporated to give the title compound (800 mg), which was used without firther purification as a white solid, m.p. 245° C. [Elemental analysis:—C,53.91; H,3.34; N,8.30%. Calculated for C22H15Cl2N3O4S:—C,54.11; H,3.10; N,8.60%].
Workup
- temperatureto warm to −20° C. over a period of 90 minutes
- customquenched with water (20 ml)
- extractionextracted three times with ethyl acetate (25 ml)
- dry with materialThe combined extracts were dried over sodium sulphate
- customthen evaporated
Sources & evidence
- ORD record
- ord-febdfdfaf906435daa06269344057913
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06303600B1
Reaction notes
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