1-(3,4-Methylenedioxvphenyl)-2-(pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline → 3-Benzo[1,3]dioxol-5-yl-2-pyrimidin-2-yl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

HRID 2415378Notes

Reaction equation

HRID 2415378 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23]3[N:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:4][C:3]=2[O:2]1.CC([O-:33])(C)C.[K+]>CN(C=O)C>[N:28]1[CH:27]=[CH:26][CH:25]=[N:24][C:23]=1[N:11]1[CH2:12][C:13]2[C:14](=[O:33])[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[NH:21][C:22]=2[CH:10]1[C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 109815071-(3,4-Methylenedioxvphenyl)-2-(pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carbolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 110254213-Benzo[1,3]dioxol-5-yl-2-pyrimidin-2-yl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3,4-methylenedioxyphenyl)-2-(pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-β-carboline (0.153 g, 0.415 mmol) (prepared as in Example 16) in anhydrous DMF (4.1 mL) was added KOtBu (0.079 g, 0.70 mmol, 1.7 eq.). After 5 min, oxygen gas was bubbled through the solution for 1 h. Diethyl ether (45 mL) was added to the reaction mixture and the supernatant decanted. Brine (2 mL) was added to the residue and the pH was adjusted to pH˜7 by addition of a few drops of 1N HCl. The water was removed in vacuo as an azeotrope with toluene. The resulting deep red residue was dissolved in a minimum amount of THF, and purified by column chromatography (silca gel; EtOH: CH2Cl2=1:9) to yield the product as a white solid.

Workup

  1. customoxygen gas was bubbled through the solution for 1 h
  2. additionDiethyl ether (45 mL) was added to the reaction mixture
  3. additionBrine (2 mL) was added to the residue
  4. additionthe pH was adjusted to pH˜7 by addition of a few drops of 1N HCl
  5. customThe water was removed in vacuo as an azeotrope with toluene
  6. dissolutionThe resulting deep red residue was dissolved in a minimum amount of THF
  7. custompurified by column chromatography (silca gel; EtOH: CH2Cl2=1:9)

Sources & evidence

ORD record
ord-3523c5bf15be476ea5d1abbccaa02270
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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