Stannous Chloride → 2-Amino-5-chloro-N-(5-chloro-quinolin-8-yl)-4-fluoro-benzenesulfonamide

HRID 513564Notes

Reaction equation

HRID 513564 reaction equation
[Cl:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([N+:23]([O-])=O)=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([Cl:22])=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)(=[O:10])=[O:9])[CH:7]=1.Cl[Sn]Cl>Cl.CCO>[NH2:23][C:5]1[CH:4]=[C:3]([F:26])[C:2]([Cl:1])=[CH:7][C:6]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:22])=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:9])=[O:10]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 681834355-Chloro-N-(5-chloro-quinolin-8-yl)-4-fluoro-2-nitro-benzenesulfonamide2×

Product 1

HCID 681832612-Amino-5-chloro-N-(5-chloro-quinolin-8-yl)-4-fluoro-benzenesulfonamideYield 77%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 5-chloro-N-(5-chloro-quinolin-8-yl)-4-fluoro-2-nitro-benzenesulfonamide (Intermediate 285) (210 mg, 5.0 mmol), SnCl2 (382 mg, 2.0 mmol), 6N HCl (4 drops) and EtOH (5 ml) for 30 h at 90° C. gave the title compound (150 mg, 77%) after purification by column chromatography with DCM as the eluent.

Workup

  1. customfor 30 h
  2. customat 90° C.

Sources & evidence

ORD record
ord-c9e78c81b2fe4ed293b1957aedcf4cc8
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…