Tert-Butyl nitrite → 4,6-Dibromo-2-(2,4-difluorophenyl)-3-methylpyridine

HRID 394166Notes

Reaction equation

HRID 394166 reaction equation
[Br:1][C:2]1[C:7](N)=[C:6]([Br:9])[C:5]([CH3:10])=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[N:3]=1.C(ON=O)(C)(C)C>C1COCC1>[Br:9][C:6]1[CH:7]=[C:2]([Br:1])[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[C:5]=1[CH3:10]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 226480972,4-Dibromo-6-(2,4-difluorophenyl)-5-methylpyridin-3-amine

Product 1

HCID 226480394,6-Dibromo-2-(2,4-difluorophenyl)-3-methylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2,4-dibromo-6-(2,4-difluorophenyl)-5-methylpyridin-3-amine (10 g, 26.4 mmol, 1 eq) in THF (100 mL) was added tert-butylnitrite (4.7 mL, 39.6 mmol, 1.5 eq). The solution warmed and gas evolution was evident. After 2 h, the mixture was heated to and maintained at 60° C. for 45 min. The mixture was cooled and concentrated in vacuo. The product was purified by flash column chromatography eluting with 2% Et2O in hexanes to give 4,6-dibromo-2-(2,4-difluorophenyl)-3-methylpyridine. Mass spectrum (ESI) 362.2 (M+1); 364.2 (M+3); 366.2 (M+5).

Workup

  1. temperatureThe solution warmed
  2. temperaturethe mixture was heated to and
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash column chromatography
  6. washeluting with 2% Et2O in hexanes

Sources & evidence

ORD record
ord-08df8454c9504f4e9919912e2880ff64
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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