HCID 67073865, compound → HCID 67074292, compound

HRID 1852392Notes

Reaction equation

HRID 1852392 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([I:32])=[CH:28][C:27]=2[F:33])[C:5]([N+:22]([O-])=O)=[C:6]([CH:21]=1)[O:7][C:8]1[C:9]([CH3:20])=[C:10]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=1>C1COCC1.CCO>[NH2:22][C:5]1[C:4]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([I:32])=[CH:28][C:27]=2[F:33])=[CH:3][C:2]([F:1])=[CH:21][C:6]=1[O:7][C:8]1[C:9]([CH3:20])=[C:10]([NH:14][S:15]([CH2:18][CH3:19])(=[O:16])=[O:17])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 67073865HCID 67073865, compound

Product 1

HCID 67074292HCID 67074292, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

1.6 g crude N-(3-{5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]-2-nitrophenoxy}-2-methylphenyl)-ethanesulfonamide (2.7 mmol, 1 eq.) were dissolved in 40 mL THF/EtOH 1:1 and treated with 3.1 g stannous chloride dihydrate (SnCl2 2H2O) (13.6 mmol, 5 eq.) and the resulting mixture was refluxed for 16 h. The reaction mixture was concentrated, the residue quenched with 26% NH3 and extracted with DCM. The combined organic layers were washed with ammonium chloride solution and saturated sodium chloride solution, dried, filtered and concentrated in vacuo. The residue was purified by flash column chromatography to give 996 mg of the target compound (65% yield).

Workup

  1. temperaturethe resulting mixture was refluxed for 16 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue quenched with 26% NH3
  4. extractionextracted with DCM
  5. washThe combined organic layers were washed with ammonium chloride solution and saturated sodium chloride solution
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-4abf83a4f25b42be804f491998c1f1d9
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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