Oxygen → HCID 12993016, compound

HRID 2415356Notes

Reaction equation

HRID 2415356 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:22]4[NH:21][C:20]5C(=[CH:16][CH:17]=[CH:18][CH:19]=5)C=4C[CH2:12][N:11]3[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.C[C:31]([CH3:34])([O-:33])[CH3:32].[K+].O=O>CN(C=O)C>[CH2:23]([N:11]1[CH2:12][C:34]2[C:31](=[O:33])[C:32]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[NH:21][C:22]=2[CH:10]1[C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 22640315HCID 22640315, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 12993016HCID 12993016, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2,3-Dihydrobenzofuran-5-yl)-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline (prepared as in Example 2) (3.10 g, 8.15 mmol) was dissolved in dry DMF (20 mL). Potassium t-butoxide (2.29 g, 20.38 mmol) was added, followed by oxygen, bubbled in via syringe needle. The solution was stirred for 1.5 h. To the reaction mixture was added a solution of HCl in ether (10 mL, 2M) and the solution dripped into rapidly stirring water. The resulting suspension was stirred overnight. A brown solid was filtered off and washed with water. The filtrate was neutralized with 1N NaOH, resulting in a yellow precipitate. The solid was filtered, washed with water, dried briefly, and partially dissolved in THF/methanol. The precipitate solid was filtered and washed with ether to yield the product as a pale yellow solid.

Workup

  1. custombubbled in via syringe needle
  2. additionTo the reaction mixture was added a solution of HCl in ether (10 mL, 2M)
  3. stirringThe resulting suspension was stirred overnight
  4. filtrationA brown solid was filtered off
  5. washwashed with water
  6. customresulting in a yellow precipitate
  7. filtrationThe solid was filtered
  8. washwashed with water
  9. customdried briefly
  10. dissolutionpartially dissolved in THF/methanol
  11. filtrationThe precipitate solid was filtered
  12. washwashed with ether

Sources & evidence

ORD record
ord-7a1e295b15eb4a21bcc174fa7862908d
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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