Triethylamine → (+/-)-(1,3,4,9-Tetrahydro-beta-carboline-2-yl)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)methanone

HRID 1987771Notes

Reaction equation

HRID 1987771 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1.C(N(CC)CC)C.[CH3:21][C:22]1([C:37](Cl)=[O:38])[CH2:26][C:25]2[C:27]([CH3:36])=[C:28]([N+:33]([O-:35])=[O:34])[C:29]([CH3:32])=[C:30]([CH3:31])[C:24]=2[O:23]1>CN(C=O)C>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:37]([C:22]1([CH3:21])[CH2:26][CH:25]2[CH:27]([CH3:36])[C:28]([N+:33]([O-:35])=[O:34])=[C:29]([CH3:32])[C:30]([CH3:31])=[C:24]2[O:23]1)=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107838Tetrahydro-beta-carbolineHCID 231183052,4,6,7-Tetramethyl-5-nitro-2,3-dihydro-1-benzofuran-2-carbonyl chloride

Product 1

HCID 68846049(+/-)-(1,3,4,9-Tetrahydro-beta-carboline-2-yl)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.5 g of 2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acid, 20 ml of methylene chloride and 0.27 g of thionyl chloride were added, followed by heating at reflux for 2 hours. After returning the temperature to room temperature, the solvent was distilled off to obtain 2,4,6,7-tetramethyl-5-nitro-2,3-dihydrobenzofuran-2-carbonyl chloride. To 0.33 g of 2,3,4,9-tetrahydro-1H-beta-carboline, 0.23 g of triethylamine and 15 ml of DMF, a solution prepared by dissolving 2,4,6,7-tetramethyl-5-nitro-2,3-dihydrobenzofuran-2-carbonyl chloride in DMF was added, followed by stirring overnight at room temperature. The mixture was poured into ice-water and a crystal was collected by filtration. The crystal was dissolved in chloroform, washed with saturated saline and dried over anhydrous magnesium sulfate and, after the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain 0.54 g of the objective product.

Workup

  1. additionwas added
  2. filtrationa crystal was collected by filtration
  3. dissolutionThe crystal was dissolved in chloroform
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationafter the solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-1e0e59e9c8bd42c79d5d45804f5f71f9
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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