Potassium Carbonate → HCID 12042502, compound

HRID 844133Notes

Reaction equation

HRID 844133 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]([CH3:13])[NH:5]2.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C(O)C.O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]([CH3:13])[NH:5]3)=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 117156816-bromo-3-methyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 12042502HCID 12042502, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 6-bromo-3-methyl-3,4-dihydro-1H-quinoxalin-2-one (2.4 g, 10 mmol), 4-chlorophenyl boronic acid (1.6 g, 10 mmol), potassium carbonate (4 g, 30 mmol), and tetrakis-(triphenylphosphine)palladium (0) in dimethoxyethane (150 ml), ethanol (25 ml), and water (25 ml) was heated to reflux for 6 hours. After cooling to room temperature the mixture was diluted with water, and extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated to obtain crude product (0.83 g, 30%). A sample was recrystallized from ethanol to afford the title compound: m.p. 228-230° C. 1H-NMR (DMSO-d6) δ1.28 (d, J=6.63 Hz, 3H), 3.83 (q, J=6.63 Hz, 1H), 6.16 (bs, 1H), 6.81 (d, J=8.00 Hz, 1H), 6.91 (dd, J=8.05, 1.9 Hz, 1H), 6.95 (d, J=1.7 Hz, 1H), 7.46 (d, J=8.6 Hz, 2H), 7.55 (d, J=8.6 Hz, 2H), 10.32 (s, 1H); MS (EI) m/z 272/274.

Workup

  1. temperatureto reflux for 6 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain crude product (0.83 g, 30%)
  8. customA sample was recrystallized from ethanol

Sources & evidence

ORD record
ord-67de80e1a3f548e8b81a757f0815ea87
Source dataset
uspto-grants-2002_04
Patent number
US06380235B1

Reaction notes

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