Pyridine-2-sulfonyl Chloride → HCID 57476199, compound

HRID 1994819Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[CH3:23][S:20]([CH2:19][CH2:18][CH2:17][O:16][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH:1][S:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=3)(=[O:32])=[O:31])[CH:3]=1)[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2)(=[O:22])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of ethyl 7-amino-5-[3-(methylsulfonyl)propoxy]-1H-indole-2-carboxylate (4.8 g) and pyridine (50 mL) was added pyridine-2-sulfonyl chloride (3.0 g) at 0° C., and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was concentrated, aqueous citric acid solution was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and saturated brine, dried (MgSO4), and concentrated. The obtained crystals were washed with diisopropyl ether, and recrystallized from acetone-hexane to give the title compound (4.68 g, yield 69%) as pale-brown prism crystals. melting point 194-195° C.

Workup

concentrationThe reaction mixture was concentrated
additionaqueous citric acid solution was added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed successively with water and saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated
washThe obtained crystals were washed with diisopropyl ether
customrecrystallized from acetone-hexane

Sources & evidence

ORD record: ord-3b42d7b2a9424fc381e2618e6ad6862c
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652133B2

Reaction notes

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