4-Toluenesulfonyl chloride → HCID 22663271, compound

HRID 2054478Notes

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

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 further 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-3f6ebf8d465d40f298c579a99340c236
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329675B2

Reaction notes

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