Sodium Methoxide → HCID 67119626, compound

HRID 574088Notes

Reaction equation

HRID 574088 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[C:14](F)[CH:13]=[C:12]([F:17])[C:11]=1[N+:18]([O-:20])=[O:19].[CH3:21][O-:22].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[C:14]([O:22][CH3:21])[CH:13]=[C:12]([F:17])[C:11]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57625029HCID 57625029, compound2×

Product 1

HCID 67119626HCID 67119626, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-N-(3,5-difluoro-2-nitrophenyl)-4-iodobenzenamine (Intermediate 14, 1.05 g, 2.7 mmol) in THF (25 mL) was added NaOMe solution (prepared by dissolving Na metal (61 mg, 2.7 mmol) in 6 mL of methanol)-78° C. The reaction mixture was brought to rt and stirred for 1 h at same temperature. The progress of reaction was monitored by TLC. After completion, the reaction mixture was quenched with water and extracted with ether. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography to yield 2-fluoro-N-(3-fluoro-5-methoxy-2-nitrophenyl)-4-iodobenzenamine as yellow solid (584 mg). 1H-NMR (400 MHz, CDCl3): δ 3.91 (3H, s), 6.23 (1H, d, J=10.4), 6.35 (1H, d, J=10.8), 7.04-7.08 (1H, m), 7.45-7.52 (2H, m), 7.83 (1H, s).

Workup

  1. customwas brought to rt
  2. customThe progress of reaction
  3. customAfter completion, the reaction mixture was quenched with water
  4. extractionextracted with ether
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-cff30d744e224d848fce98cc9af61bda
Source dataset
uspto-grants-2015_05
Patent number
US09034861B2

Reaction notes

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