N-bromobutanimide → HCID 89485613, compound

HRID 1469391Notes

Reaction equation

HRID 1469391 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:12]=2)=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O>ClCCl>[Br:19][C:10]1[S:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:12][C:11]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58581706HCID 58581706, compound

Product 1

HCID 89485613HCID 89485613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[2-(4-Fluoro-phenyl)-1,3-thiazol-4-yl]pyridine from step 1 (400 mg, 1.56 mmol) was dissolved in dichloromethane (10 mL), and N-bromosuccinimide (330 mg, 1.87 mmol) was added. The reaction was stirred at room temperature for 2 h. Then the solution was washed with water, and dried (Na2SO4). The drying agent was filtered off, and the filtrate was concentrated. The resulting residue was purified on a silica gel flash chromatography column eluted with 0-20% EtOAc-hexane to give the title compound. LC-MS m/z 337.0 [M+1]+.

Workup

  1. washThen the solution was washed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationThe drying agent was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified on a silica gel flash chromatography column
  6. washeluted with 0-20% EtOAc-hexane

Sources & evidence

ORD record
ord-22eb44f356ec4ac58fc0416f268cbf55
Source dataset
uspto-grants-2015_04
Patent number
US09006268B2

Reaction notes

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