5-methyl-4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde → 5-Methyl-1-(2-oxo-4-piperidin-4-yl-1,2-dihydroindol-3-ylidene-methyl)-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one

HRID 988178Notes

Reaction equation

HRID 988178 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:16])[NH:11]3)[CH2:3][CH2:2]1.[CH3:17][N:18]1[CH2:23][CH2:22][C:21]2=[C:24]([CH:27]=O)[NH:25][CH:26]=[C:20]2[C:19]1=[O:29]>N1CCCCC1.C(O)C>[CH3:17][N:18]1[CH2:23][CH2:22][C:21]2=[C:24]([CH:27]=[C:9]3[C:8]4[C:12](=[CH:13][CH:14]=[CH:15][C:7]=4[CH:4]4[CH2:3][CH2:2][NH:1][CH2:6][CH2:5]4)[NH:11][C:10]3=[O:16])[NH:25][CH:26]=[C:20]2[C:19]1=[O:29]

Participants

5

Reactant 2

HCID 99205265-methyl-4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehydeHCID 221353964-(Piperidin-4-yl)indolin-2-one

Product 1

HCID 695841735-Methyl-1-(2-oxo-4-piperidin-4-yl-1,2-dihydroindol-3-ylidene-methyl)-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-oneYield 57.1%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-piperidin-4-yl-1,3-dihydroindol-2-one (58.4 mg, 0.27 mmol), 5-methyl-4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde (48 mg, 0.27 mmol) and piperidine (1 drop) in ethanol (1 mL) was stirred at room temperature for 7 days. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 58 mg (57%) of the title compound as a yellow solid.

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-5953f9e269d345c7b5c12457f06ec8c7
Source dataset
uspto-grants-2003_10
Patent number
US06635640B2

Reaction notes

Loading…