Piperidine → HCID 69811336, compound

HRID 1615273Notes

Reaction equation

HRID 1615273 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH: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](/[CH:7]=[CH:8]/[C:9]2[C:17]3[C:12](=[CH:13][C:14](/[CH:18]=[C:30]4/[C:29](=[O:37])[NH:28][C:36]5[C:31]/4=[CH:32][CH:33]=[CH:34][CH:35]=5)=[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 86651957HCID 86651957, compound

Product 1

HCID 69811336HCID 69811336, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (E)-3-(2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (927 mg, 2.44 mmol), oxindole (325 mg, 2.44 mmol) and MeOH (20 mL) was added piperidine (24 uL, 0.244 mmol) and the reaction heated to 60° C. for 4 hours. A yellow precipitate crashed out of the reaction medium which was filtered and washed with MeOH to give the title compound (960 mg, 79%) as a yellow solid. MS ESI 495.3 [M+H]+, calcd for [C29H30N4O2Si+H]+ 495.22.

Workup

  1. filtrationwas filtered
  2. washwashed with MeOH

Sources & evidence

ORD record
ord-e58a503efd9049c38bd5a258fbe4580d
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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