Pyridine → HCID 60531925, compound

HRID 513539Notes

Reaction equation

HRID 513539 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[S:11](Cl)(=[O:13])=[O:12].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[S:11]([NH:8][C:4]1[CH:3]=[CH:2][CH:1]=[C:19]2[C:20]=1[N:15]=[CH:16][CH:17]=[CH:18]2)(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 1049PyridineHCID 122159422-Methyl-6-nitrobenzene-1-sulfonyl chloride2×

Product 1

HCID 60531925HCID 60531925, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoqunoline (1.6 g, 11.1 mmol), 2-methyl-6-nitro-benzenesulfonyl chloride (Intermediate 451) (3.5 g, 14.4 mmol), pyridine (10 ml), DMAP (cat.) and DCM (5 ml) gave the title compound (1.5 g, 39%) after purification by column chromatography with n-hexane/EtOAc (85:15) as the eluent.

Sources & evidence

ORD record
ord-ea8b610daba949a79b736186ff840896
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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