Quinoline → (Z)-tert-butyl 4-(1-(4-methoxybenzyl)-3-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)vinyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387551Notes

Reaction equation

HRID 387551 reaction equation
[CH3:1][O:2][C:3]1[CH:53]=[CH:52][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:16]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[C:11]3[C:10]([C:36]#[C:37][C:38]3[CH:39]=[N:40][N:41]([CH2:43][C:44]4[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=4)[CH:42]=3)=[N:9]2)=[CH:5][CH:4]=1.N1C2C(=CC=CC=2)C=CC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:16]([N:17]4[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:21][CH2:22]4)=[C:11]3[C:10](/[CH:36]=[CH:37]\[C:38]3[CH:39]=[N:40][N:41]([CH2:43][C:44]4[CH:45]=[CH:46][C:47]([O:50][CH3:51])=[CH:48][CH:49]=4)[CH:42]=3)=[N:9]2)=[CH:52][CH:53]=1

Participants

6

Reactant 2

HCID 7047QuinolineHCID 68768812tert-butyl 4-(1-(4-methoxybenzyl)-3-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethynyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 68757876(Z)-tert-butyl 4-(1-(4-methoxybenzyl)-3-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)vinyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylateYield 74%

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(1-(4-methoxybenzyl)-3-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethynyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.12 g, 0.169 mmol), quinoline (0.011 g, 0.085 mmol) and Lindlar's Catalyst (0.18 g, 0.085 mmol) in MeOH (3 mL) and benzene (3 mL) was charged with 1 atmosphere H2 and stirred at room temperature for 6 hours. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo, and the residue obtained was purified flash chromatography on silica gel (hexane:ethyl acetate=1:1) to give (Z)-tert-butyl 4-(1-(4-methoxybenzyl)-3-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)vinyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.089 g, 74%) as a solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue obtained
  5. customwas purified flash chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-dc11442462d242cba76373bb79dd0c07
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

Loading…