Triethylamine → HCID 69068620, compound

HRID 229386Notes

Reaction equation

HRID 229386 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][CH:14]=[C:7]1[CH:6]([CH3:15])[NH:5]2.[C:16](Cl)(=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][CH:14]=[C:7]1[CH:6]([CH3:15])[N:5]2[C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 69069638HCID 69069638, compound

Product 1

HCID 69068620HCID 69068620, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 7-bromo-4-methyl-4,5-dihydropyrrolo[1,2-a]quinoxaline (225 mg, 0.86 mmol) in methylene chloride (4 mL), under nitrogen, was treated with m-anisoyl chloride (219 mg, 1.28 mmol) followed by triethyl amine (0.24 mL, 1.72 mmol). The reaction was stirred at 25° C. for 15 h, after which time the reaction was washed with a saturated aqueous solution of sodium bicarbonate, and the reaction mixture was concentrated in vacuo. The product was purified via Biotage Horizon® (25S, silica, gradient from 5% EtOAc/hexane to 40% EtOAc/hexane) to yield 287 mg (84%) of 7-bromo-5-(3-methoxybenzoyl)-4-methyl-4,5-dihydropyrrolo[1,2-a]quinoxaline as a white foam. MS (ESI) m/z 397/399 ([M+H]+); HRMS: calcd for C20H17BrN2O2, 396.0473; found (ESI+), 397.05389.

Workup

  1. washafter which time the reaction was washed with a saturated aqueous solution of sodium bicarbonate
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe product was purified via Biotage Horizon® (25S, silica, gradient from 5% EtOAc/hexane to 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-420c96d0d28c4c42872955efb93b44cd
Source dataset
uspto-grants-2009_07
Patent number
US07563793B2

Reaction notes

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