Potassium Bicarbonate → 3-Bromo-5-(4-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butyl)-4,5-dihydroisoxazole

HRID 517915Notes

Reaction equation

HRID 517915 reaction equation
[CH2:1]([N:7]1[C:12]2=[N:13][C:14]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[N:16]=[C:11]2[CH2:10][CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C(=O)([O-])O.[K+].[Br:36][C:37](Br)=[N:38][OH:39]>CCOC(C)=O>[Br:36][C:37]1[CH2:6][CH:5]([CH2:4][CH2:3][CH2:2][CH2:1][N:7]2[C:12]3=[N:13][C:14]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)=[C:15]([C:17]4[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=4)[N:16]=[C:11]3[CH2:10][CH2:9][CH2:8]2)[O:39][N:38]=1

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromideHCID 896901775-(Hex-5-enyl)-2,3-dip-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine2×

Product 1

HCID 896903823-Bromo-5-(4-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butyl)-4,5-dihydroisoxazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture comprising 5-(hex-5-enyl)-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate H) (3.98 g, 10 mmol) and potassium hydrogen carbonate (5.01 g, 50.0 mmol) in EtOAc (50 ml) was treated dropwise with dibromoformaldoxime (6.08 g, 30.0 mmol) in EtOAc (50 ml) over 2 hours. The mixture was stirred at room temperature overnight and then filtered. The filtrate was washed with 1H HCl, water, brine and dried by passing through a phase separator. The solvent was removed under reduced pressure to afford the titled compound which was used without further purification.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 1H HCl, water, brine
  3. customdried
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e449091dabbd4134ac8d36a5a41f4c7b
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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