N-bromobutanimide → HCID 66977376, compound

HRID 712167Notes

Reaction equation

HRID 712167 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=1.C1C(=O)N([Br:28])C(=O)C1>C(O)(=O)C>[Br:28][C:3]1[C:2]([F:1])=[CH:7][C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:11])[CH3:12])=[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66977380HCID 66977380, compound

Product 1

HCID 66977376HCID 66977376, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(5-fluoro-2-(pyridin-2-yl)phenyl)pivalamide (19.0 g, 69.83 mmol) in acetic acid (140.0 mL) was added NBS (24.86 g, 139.66 mmol) at 0° C. The resulted mixture was stirred at 50° C. for 1 h. After completion of reaction (by TLC), the mixture was poured onto 100 mL of crushed ice and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and solvent evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 2% EtOAc:hexane to obtain the desired product as an off white solid (17.50 g, 72%).

Workup

  1. customAfter completion of reaction (by TLC)
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4 and solvent
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-71bd42ae0f674826a9ffb48012d15528
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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