4-(Chlorosulfonyl)benzoic acid → HCID 10641632, compound

HRID 1173110Notes

Reaction equation

HRID 1173110 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][CH:21]=[C:20]2[Cl:24]>N1C=CC=CC=1>[Cl:24][C:20]1[C:19]2[C:23](=[C:15]([NH:14][S:2]([C:5]3[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=3)(=[O:4])=[O:3])[CH:16]=[CH:17][CH:18]=2)[NH:22][CH:21]=1

Participants

4

Reactant 2

HCID 823854-(Chlorosulfonyl)benzoic acidHCID 110082903-chloro-1H-indol-7-amine

Product 1

HCID 10641632HCID 10641632, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.82 g (12.8 mmol) of 4-(chlorosulfonyl)benzoic acid and 1.42 g (8.54 mmol) of 7-amino-3-chloro-1H-indole were reacted with each other in pyridine at room temperature under stirring overnight, to give 2.33 g of 4-[N-(3-chloro-1H-indole-7-yl)sulfamoyl]benzoic acid. To 303 mg (0.86 mmol) of the product were successively added 260 μl of dimethylformamide, 204 μl (0.95 mmol) of diphenylphosphorylazide, 132 μl (0.95 mmol) of triethylamine and 113 μl (0.94 mmol) of 2-(2-aminoethyl)pyridine, followed by stirring at room temperature overnight. After concentrating, ethyl acetate and an aqueous saturated sodium bicarbonate were added thereto. The organic layer was separated and washed with brine. After evaporating the solvent, the residue was purified by silica gel column chromatography, to give 175 mg of the title compound.

Sources & evidence

ORD record
ord-4fb1ec3fa2a048a7b304202f3bf1c34c
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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