Sodium hydride → HCID 23003170, compound

HRID 552265Notes

Reaction equation

HRID 552265 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[CH3:15])[N:3]=1.[F:16][C:17]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:18]=1N.[H-].[Na+]>O1CCCC1.[NH4+].[Cl-]>[F:16][C:17]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:18]=1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[CH3:15])[N:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 796472,6-DifluoroanilineHCID 23003169HCID 23003169, compound

Product 1

HCID 23003170HCID 23003170, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

In a 50 ml round-bottomed flask, 550 mg (2.07 mmol) of 2-bromo-6-(4-fluoro-2-methylphenyl)pyridine produced in step B was dissolved in 30 ml of anhydrous tetrahydrofuran forming a clear, colorless solution. 2,6-difluoroaniline (2.14 ml, 2.14 mmol) was added followed by 112 mg (2.79 mmol) of a 60% NaH suspension in mineral oil. Gas evolution was observed along with a mild exotherm. The solution was heated to reflux overnight and then cooled. The reaction mixture was poured in 10% NH4Cl and extracted with CH2Cl2. The organic extract was dried (MgSO4) and evaporated in vacuo to afford a brown oil that was a mixture of the product and starting material. The material was chromatographed on a short column of silica gel using 50% CH2Cl2/hexane to afford 262 mg (40%) of 2-(2,6-difluorophenyl)-6-(4-fluoro-2-methylphenyl)pyridine as a colorless oil.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. extractionextracted with CH2Cl2
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated in vacuo
  8. customto afford a brown oil that
  9. additiona mixture of the product
  10. customThe material was chromatographed on a short column of silica gel using 50% CH2Cl2/hexane

Sources & evidence

ORD record
ord-3ee03bfee33a4c7a9d16ef7bf661cf0e
Source dataset
uspto-grants-2011_05
Patent number
US07951809B2

Reaction notes

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