Sodium Dithionite → HCID 86669372, compound

HRID 574097Notes

Reaction equation

HRID 574097 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[C:13]([F:18])[CH:12]=[C:11]([O:19][CH3:20])[C:10]=2[F:21])=[C:4]([F:22])[CH:3]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([NH2:15])=[C:13]([F:18])[CH:12]=[C:11]([O:19][CH3:20])[C:10]=2[F:21])=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 86669364HCID 86669364, compound2×

Product 1

HCID 86669372HCID 86669372, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of (4-bromo-2-fluoro-phenyl)-(2,5-difluoro-3-methoxy-6-nitro-phenyl)-amine (Intermediate 16, 0.850 g, 2.2 mmol) in ethanol (13 mL) was stirred at 70° C. to obtain a clear solution. To this hot solution, was added a freshly prepared solution of Na2S2O4 (1.2 g, 6.7 mmol) in water (2.4 mL) and stirred the reaction mixture at 90° C. for 1 h. The progress of reaction was monitored by TLC. After completion, the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with water, and the organic phase was dried over anhydrous Na2SO4 and concentrated to yield N2-(4-bromo-2-fluoro-phenyl)-3,6-difluoro-4-methoxy-benzene-1,2-diamine as a brown solid (600 mg). 1H-NMR (400 MHz, CDCl3): δ 3.61 (2H, bs), 3.82 (3H, s), 5.40 (1H, bs), 6.37 (1H, t), 6.68-6.73 (1H, m), 7.06 (1H, d, J=8.4), 7.24 (1H, d, J=14).

Workup

  1. customto obtain a clear solution
  2. stirringstirred the reaction mixture at 90° C. for 1 h
  3. customThe progress of reaction
  4. customAfter completion, the solvent was removed under reduced pressure
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialthe organic phase was dried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-31c850c459e6427899a47c9e6d02d94e
Source dataset
uspto-grants-2015_05
Patent number
US09034861B2

Reaction notes

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