Sodium Dithionite → HCID 68360910, compound

HRID 1852400Notes

Reaction equation

HRID 1852400 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([I:38])=[CH:34][C:33]=2[F:39])[C:5]([N+:28]([O-])=O)=[C:6]([CH:27]=1)[O:7][C:8]1[CH:9]=[C:10]([CH:24]=[CH:25][CH:26]=1)[CH2:11][NH:12][S:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:15])=[O:14].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[NH2:28][C:5]1[C:4]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([I:38])=[CH:34][C:33]=2[F:39])=[CH:3][C:2]([F:1])=[CH:27][C:6]=1[O:7][C:8]1[CH:9]=[C:10]([CH:24]=[CH:25][CH:26]=1)[CH2:11][NH:12][S:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 68360801HCID 68360801, compound

Product 1

HCID 68360910HCID 68360910, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.08 g of tert-butyl [(3-{5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]-2-nitrophenoxy}benzyl)sulfamoyl]carbamate (4.55 mmol, 1 eq.) were dissolved in 88 mL THF and heated to 50° C. upon which a solution of 13.5 g sodium dithionite (77.4 mmol, 17 eq.) in 70 mL water was added and stirring was continued at that temperature for 5 h. The layers were separated and the THF layer was concentrated in vacuo. The residue was taken up in ethyl acetate, washed with sodium bicarbonate solution and sodium chloride solution, dried, filtered and concentrated in vacuo. The residue was further purified by flash column chromatography (hexan to hexan/ethyl acetate 1:1 gradient) to yield 886 mg (30% yield) of the target compound (as a 2-3:1 regioisomeric mixture).

Workup

  1. additionwas added
  2. customThe layers were separated
  3. concentrationthe THF layer was concentrated in vacuo
  4. washwashed with sodium bicarbonate solution and sodium chloride solution
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was further purified by flash column chromatography (hexan to hexan/ethyl acetate 1:1 gradient)

Sources & evidence

ORD record
ord-25939dcbdb0e4cb99ce2513e0de43d6a
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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