N-bromobutanimide → HCID 57963064, compound

HRID 1396147Notes

Reaction equation

HRID 1396147 reaction equation
[F:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(#N)C>[Br:18][C:3]1[CH:4]=[CH:5][C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:7][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 17965116HCID 17965116, compound

Product 1

HCID 57963064HCID 57963064, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (6-fluoro-pyridin-2-yl)-(4-methoxy-benzyl)-amine (41, 151 g, 650 mmol) in 4 L of acetonitrile under an atmosphere of nitrogen, N-bromosuccinimide (116 g, 650 mmol) is added in portions. After reacting for 2 hours, the solvent is removed under vacuum and the residue is taken up in ethyl acetate, then poured into aqueous sodium thiosulfate. The organic layer is washed with warm water, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is crystallized from heptane to provide the desired compound (42, 172 g, 553 mmol, 85% yield).

Workup

  1. customthe solvent is removed under vacuum
  2. additionpoured into aqueous sodium thiosulfate
  3. washThe organic layer is washed with warm water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material is crystallized from heptane

Sources & evidence

ORD record
ord-baca0cb2f0d54e84a1b4f3ae74eda575
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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