N-bromobutanimide → HCID 22281740, compound

HRID 1725338Notes

Reaction equation

HRID 1725338 reaction equation
C([O:5][C:6]([C:8]1[C:17]2[C:12](=[C:13]([F:20])[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][CH:9]=1)=[CH2:7])CCC.[Br:21]N1C(=O)CCC1=O>C1COCC1.O>[Br:21][CH2:5][C:6]([C:8]1[C:17]2[C:12](=[C:13]([F:20])[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68845177HCID 68845177, compound

Product 1

HCID 22281740HCID 22281740, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

9.0 g (32.7 mmol) of 4-(1-Butoxy-vinyl)-8-fluoro-6-methoxy-quinoline was dissolved in 200 mL of 3:1 THF/water. 6.4 g of N-bromosuccinimide was added and the contents stirred at rt for 3 hrs. Solvent was then removed by rotary-evaporation. The crude material was purified by flash chromatography on silica gel using 20% ethyl acetate/hexanes as the eluent to give 8.5 g (88%) of the desired product. 1H NMR (CDCl3, 400 MHz) 8.92 (d, 1H), 7.71 (m, 2H), 7.18 (d, 1H), 4.55 (s, 2H), 3.94 (s, 3H).

Workup

  1. customSolvent was then removed by rotary-evaporation
  2. customThe crude material was purified by flash chromatography on silica gel using 20% ethyl acetate/hexanes as the eluent

Sources & evidence

ORD record
ord-325914b3ad0440158568902a14373f2c
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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