N-bromobutanimide → HCID 67000967, compound

HRID 558612Notes

Reaction equation

HRID 558612 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.C1C(=O)N([Br:25])C(=O)C1.C([O-])(O)=O.[Na+]>C(#N)C>[Br:25][C:11]1[C:12]([NH2:15])=[N:13][CH:14]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:8][CH:7]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 20099814HCID 20099814, compound

Product 1

HCID 67000967HCID 67000967, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 5-(4-trifluoromethyl-phenyl)-pyridin-2-ylamine (example C.25 step 1) (3.9 g, 16 mmol) in acetonitrile (65 mL) at 0° C. was added NBS (2.914 g, 16 mmol) and the mixture was stirred at 23° C. for 2 h. Poured on ice with sat. NaHCO3-sol., extracted thrice with AcOEt, dried the combined organic layers over Na2SO4, filtered off and evaporated. The residue was purified by silica gel column chromatography with AcOEt followed by trituration with heptane and very little ether to give the title compound as a light brown solid (3.7 g, 71%). MS (ISP) 317 [(M+H)+], 319 [(M+2+H)+].

Workup

  1. customat 0° C.
  2. extraction, extracted thrice with AcOEt
  3. dry with materialdried the combined organic layers over Na2SO4
  4. filtrationfiltered off
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography with AcOEt

Sources & evidence

ORD record
ord-e28bd1b298be444cb4d486959dc4f6ae
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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