Stannous Chloride → HCID 68183380, compound

HRID 513569Notes

Reaction equation

HRID 513569 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-])=O)(=[O:15])=[O:14])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.Cl[Sn]Cl>Cl.CCO>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:10]1[CH:11]=[C:2]([F:1])[CH:3]=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 68183129HCID 68183129, compound2×

Product 1

HCID 68183380HCID 68183380, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, N-(6-fluoro-quinolin-8-yl)-2-nitro-benzenesulfonamide (Intermediate 244) (520 mg, 1.49 mmol), SnCl2 (983 mg, 5.99 mmol), 6N HCl (3 drops) and EtOH (10 ml) for 4 h at 80° C. gave the title compound (410 mg, 86%) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

Workup

  1. customfor 4 h
  2. customat 80° C.

Sources & evidence

ORD record
ord-0327f98c0312425ea6ff602fe7ab245c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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