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

HRID 988177Notes

Reaction equation

HRID 988177 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.[O:17]=[C:18]1[C:23]2=[CH:24][NH:25][C:26]([CH:27]=O)=[C:22]2[CH2:21][CH2:20][NH:19]1>N1CCCCC1.C(O)C>[O:16]=[C:10]1[C:9](=[CH:27][C:26]2[NH:25][CH:24]=[C:23]3[C:22]=2[CH2:21][CH2:20][NH:19][C:18]3=[O:17])[C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[CH:4]2[CH2:3][CH2:2][NH:1][CH2:6][CH2:5]2)[NH:11]1

Participants

5

Reactant 2

HCID 99641894-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehydeHCID 221353964-(Piperidin-4-yl)indolin-2-one

Product 1

HCID 695841271-(2-Oxo-4-piperidin-4-yl-1,2-dihydroindol-3-ylidenemethyl)-2,5,6,7-tetrahydropyrrolo[3,4-c]pyridin-4-oneYield 27.6%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-piperidin-4-yl-1,3-dihydroindol-2-one (79 mg, 0.36 mmol), 4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde (50 mg, 0.3 mmol) and piperidine (1 drop) in ethanol (2 mL) was stirred at room temperature for 4 days. The precipitate was collected by vacuum filtration, washed with ethanol followed by 0.1% of acetic acid in water and dried to give 30 mg (23%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-a33a28116d7140bd9a1a66e870525393
Source dataset
uspto-grants-2003_10
Patent number
US06635640B2

Reaction notes

Loading…