N-bromobutanimide → HCID 66781369, compound

HRID 1095674Notes

Reaction equation

HRID 1095674 reaction equation
[Si]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](/[CH:19]=[CH:20]/OC)[CH:15]=[CH:14]2)(C(C)(C)C)(C)C.BrN1C(=O)CCC1=O.[CH3:31][O:32][CH2:33][CH2:34][O:35][C:36]1[CH:41]=[CH:40][N:39]=[C:38]([NH2:42])[CH:37]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[CH3:31][O:32][CH2:33][CH2:34][O:35][C:36]1[CH:41]=[CH:40][N:39]2[C:19]([C:16]3[CH:15]=[CH:14][C:13]4[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=4)[N:17]=3)=[CH:20][N:42]=[C:38]2[CH:37]=1

Participants

7

Reactant 4

HCID 67184N-bromobutanimideHCID 2724141Tetrabutylammonium FluorideHCID 667820424-(2-Methoxyethoxy)pyridin-2-amineHCID 66782157HCID 66782157, compound

Product 1

HCID 66781369HCID 66781369, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

(E)-8-(tert-butyldimethylsilyloxy)-2-(2-methoxyvinyl)quinoline (1.90 g, 6.02 mmol) was dissolved in a solution of THF (20 mL) and water (3 mL). N-bromosuccinimide (1.13, 6.32 mmol) was added to the reaction mixture. After the reaction was judged to be complete (monitored by MS), 4-(2-methoxyethoxy)pyridin-2-amine 1.01 g, 6.02 mmol) was added. The reaction was then heated to reflux for 5 hours and then cooled to ambient temperature. To the reaction mixture was added 10 ml of 1.0 M tetrabutylammonium fluoride in THF. The reaction mixture was stirred at ambient temperature for 1 hour and then diluted with water. The mixture was extracted with 1:4 isopropyl acetate:dichloromethane. The combined organic phase was dried (sodium sulfate), filtered and condensed under reduced pressures. The residue was purified by flash chromatography, eluting with gradient from 100% EtOAc to 10% MeOH (w/6% NH4OH)/EtOAc to obtain 700 mg of the desired product as a red solid.

Workup

  1. additionwas added
  2. temperatureThe reaction was then heated
  3. temperatureto reflux for 5 hours
  4. extractionThe mixture was extracted with 1:4 isopropyl acetate
  5. dry with materialThe combined organic phase was dried (sodium sulfate)
  6. filtrationfiltered
  7. customcondensed under reduced pressures
  8. customThe residue was purified by flash chromatography
  9. washeluting with gradient from 100% EtOAc to 10% MeOH (w/6% NH4OH)/EtOAc

Sources & evidence

ORD record
ord-93c6a6ec190c4de49a8fc65ee89ee0d8
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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