1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-bromo-2-(2,4-dimethoxybenzyl)-4-(4-nitrobenzyl)pyrrolo[1,2-a]pyrazin-1(2H)-one

HRID 2096280Notes

Reaction equation

HRID 2096280 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([N:9]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])[CH2:10][C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:8])[NH:5][CH:6]=1.N12CCCN=C1CCCCC2>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:7](=[O:8])[N:9]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=3[O:31][CH3:32])[CH:10]=[C:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[N:5]2[CH:6]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 674410924-bromo-N-(2,4-dimethoxybenzyl) N-(3-(4-nitrophenyl)prop-2-ynyl)-1H-pyrrole-2-carboxamide

Product 1

HCID 674411597-bromo-2-(2,4-dimethoxybenzyl)-4-(4-nitrobenzyl)pyrrolo[1,2-a]pyrazin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of EXAMPLE 23C (10 g, 20 mmol in dry dichloromethane (150 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.22 g, 8 mmol). The mixture was heated under reflux for 6 hours. After cooling, the reaction mixture was diluted with dichloromethane, and then washed with 0.5 N aqueous HCl (300 mL) and brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (1% methanol in CH2Cl2) to afford the title compound. LC-MS (ESI): m/z 500, 498 (M+H), RT: 2.29 min; 1H NMR (400 MHz, dimethylsulfoxide-d6): δ 3.74 (s, 3H), 3.75 (s, 3H), 4.21 (s, 2H), 4.87 (s, 2H), 6.47 (dd, J=6, 2.4 Hz, 1H), 6.56 (d, J=2.4 Hz, 1H), 6.69 (s, 1H), 6.99 (d, J=1.6 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.60 (d, J=8.8 Hz, 2H), 8.20 (d, J=8.4 Hz, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. washwashed with 0.5 N aqueous HCl (300 mL) and brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (1% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-dcc99b1df95643ecbb19f90b48cdf5d3
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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