Sodium Methoxide → HCID 86669363, compound

HRID 574086Notes

Reaction equation

HRID 574086 reaction equation
[F:1][C:2]1[C:7](F)=[CH:6][C:5]([F:9])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=1[F:21].[CH3:22][O-:23].[Na+]>C1COCC1.CO>[F:1][C:2]1[C:7]([O:23][CH3:22])=[CH:6][C:5]([F:9])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=1[F:21]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 574300722,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline2×

Product 1

HCID 86669363HCID 86669363, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitrobenzenamine (Intermediate 12. 700 mg, 1.7 mmol) in THF (20 mL) was added NaOMe solution at −78° C. (which was prepared by dissolving Na metal (39 mg, 1.7 mmol) in 4 mL of methanol). 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 under reduced pressure. The residue was purified by flash column chromatography to yield 2,5-difluoro-N-(2-fluoro-4-iodophenyl)-3-methoxy-6-nitrobenzenamine as yellow solid (597 mg). 1H-NMR (400 MHz, CDCl3): δ 3.95 (3H, s), 6.51-6.56 (1H, m), 6.57-6.65 (1H, m), 7.34 (1H, d, J=8.8), 7.42 (1H, dd, J=1.6, 10), 7.7 (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 under reduced pressure
  7. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-ad7816d2c0234aa2b32503719067e077
Source dataset
uspto-grants-2015_05
Patent number
US09034861B2

Reaction notes

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