Water → HCID 86652215, compound

HRID 217276Notes

Reaction equation

HRID 217276 reaction equation
[F:1][CH:2]([F:10])[C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[Br:11]N1C(=O)CCC1=O.O>C(#N)C>[Br:11][C:7]1[C:6]([NH2:9])=[CH:5][CH:4]=[C:3]([CH:2]([F:10])[F:1])[N:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 552816746-(Difluoromethyl)pyridin-3-amine

Product 1

HCID 86652215HCID 86652215, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the compound obtained in Step D (2.1 g) and N-bromo-succinimide (2.56 g) in acetonitrile (50 ml) was stirred at 0° C. for 10 minutes. The reaction mixture was poured into water and extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and then concentrated in vacuo. Chromatography on silica gel (eluent: hexane/ethyl acetate 1:1) afforded 2-bromo-6-difluoromethyl-pyridin-3-yl-amine (2.5 g) as a solid. MS (ES+) 223/225 (MH+); 1H NMR (400 MHz, CDCl3) 4.38 (br s, 2H), 6.52 (t, 1H), 7.08 (d, 1H), 7.41 (d, 1H).

Workup

  1. extractionextracted several times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72cca2efee3a4e69b84cf0afdc5b8c6e
Source dataset
uspto-grants-2012_06
Patent number
US08193362B2

Reaction notes

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