Sodium Dithionite → HCID 68360773, compound

HRID 1852394Notes

Reaction equation

HRID 1852394 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])[C:16]=2[N+:31]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])[C:16]=2[NH2:31])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 68360870HCID 68360870, compound

Product 1

HCID 68360773HCID 68360773, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.35 g of tert-butyl(3-{5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]-2-nitrophenoxy}phenyl)carbamate (2.3 mmol, 1 eq.) were dissolved in 43 mL THF and heated to 50° C. upon which a solution of 6.8 g sodium dithionite (39 mmol, 17 eq.) in 35 mL water was added and stirring was continued at that temperature for 1 h. The layers were separated and the aqueous layer was reextracted with ethyl acetate. The combined organic layers were dried, filtered and concentrated in vacuo. The crude product (1.5 g) was used without further purification.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product (1.5 g) was used without further purification

Sources & evidence

ORD record
ord-78a28a9052f746519426fb9ddd593fe2
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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