Pyridine → 5-Chloro-N-(5-chloro-quinolin-8-yl)-4-fluoro-2-nitro-benzenesulfonamide

HRID 513527Notes

Reaction equation

HRID 513527 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl:13][C:14]1[C:15]([F:27])=[CH:16][C:17]([N+:24]([O-:26])=[O:25])=[C:18]([S:20](Cl)(=[O:22])=[O:21])[CH:19]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:13][C:14]1[C:15]([F:27])=[CH:16][C:17]([N+:24]([O-:26])=[O:25])=[C:18]([S:20]([NH:12][C:9]2[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]3[C:8]=2[N:7]=[CH:6][CH:5]=[CH:4]3)(=[O:22])=[O:21])[CH:19]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2248605-Chloroquinolin-8-amine2×HCID 866697525-Chloro-4-fluoro-2-nitrobenzene-1-sulfonyl chloride2×

Product 1

HCID 681834355-Chloro-N-(5-chloro-quinolin-8-yl)-4-fluoro-2-nitro-benzenesulfonamideYield 12%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, using 5-chloro-quinolin-8-ylamine (Intermediate 27) (750 mg, 4.2 mmol), 5-chloro-4-fluoro-2-nitro-benzenesulfonyl chloride (Intermediate 218) (1.5 g, 5.4 mmol), DMAP (cat), pyridine (8 ml) and DCM (15 ml) gave the title compound (210 mg, 12%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-58eb0219c1cd44f6a8d948ffeae68c82
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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