Piperidine → HCID 68758106, compound

HRID 1615280Notes

Reaction equation

HRID 1615280 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]=O)=[CH:15][CH:16]=3)[N:11]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:10]=2)=[CH:3][CH:2]=1.[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][C:29]1=[O:37].N1CCCCC1>CO>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]=[C:30]4[C:31]5[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=5)[NH:28][C:29]4=[O:37])=[CH:15][CH:16]=3)[N:11]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:10]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 86651959HCID 86651959, compound

Product 1

HCID 68758106HCID 68758106, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(2-(pyridin-4-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (54 mg, 0.142 mmol), oxindole (19 mg, 0.142 mmol) in MeOH (2.0 mL) was treated with piperidine (1.5 uL, 0.0142 mmol) and the reaction heated to 60° C. and stirred for 4 hours at which time the solvent was removed and the residue purified by column chromatography (silica gel, 96:4 CH2Cl2/MeOH) to give the title compound (57 mg, 80%) as a yellow film. MS ESI 497.2 [M+H]+, calcd for [C29H32N4O2Si+H]+ 497.24.

Workup

  1. customwas removed
  2. customthe residue purified by column chromatography (silica gel, 96:4 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-20f7464dce1f40d1aeebada8cceeccc1
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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