N-bromobutanimide → HCID 58670137, compound

HRID 2249497Notes

Reaction equation

HRID 2249497 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:14][C:11]1[C:10]([NH2:13])=[CH:9][CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27628776-Phenylpyridin-3-amine

Product 1

HCID 58670137HCID 58670137, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1B (85 mg, 0.5 mmol) in DMF (1 mL) at RT was added N-bromosuccinimide (89 mg, 0.5 mmol). The reaction was stirred at RT for 16 h. After this time, no starting material was detected by LC-MS. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with saturated NaCl, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica gel (10 g) column chromatography, eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as a light brown foam (100 mg, 80%). LC/MS (method A): retention time=2.96 min, (M+H)+=249. 1H NMR (CDCl3, 400 MHz): δ 7.80-7.91(m, 2H), 7.50 (d, J=8.2 Hz, 1H), 7.38-7.44 (m, 2H), 7.31-7.35 (m, 1H), 7.05 (d, J=8.2 Hz, 1H), 4.15 (s, 2H).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined organic layers were washed with saturated NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel (10 g) column chromatography
  7. washeluting with a gradient of EtOAc (0-60%) in hexane

Sources & evidence

ORD record
ord-b168b9ed6e4f46348016e5268a1bae21
Source dataset
uspto-grants-2008_01
Patent number
US07314882B2

Reaction notes

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