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Water → 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

HRID 387550
Notes
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Reaction equation

HRID 387550 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:7]=1)#[CH:2].I[C:18]1[C:26]2[C:21](=[N:22][CH:23]=[C:24]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:25]=2[N:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)[N:20]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)[N:19]=1.O.C(OCC)(=O)C>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:54][O:53][C:50]1[CH:51]=[CH:52][C:47]([CH2:46][N:20]2[C:21]3=[N:22][CH:23]=[C:24]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:25]([N:27]4[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[CH2:29][CH2:28]4)=[C:26]3[C:18]([C:2]#[C:1][C:3]3[CH:4]=[N:5][N:6]([CH2:8][C:9]4[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=4)[CH:7]=3)=[N:19]2)=[CH:48][CH:49]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 574219374-Ethynyl-1-(4-methoxybenzyl)-1H-pyrazoleHCID 68760648tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 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
Yield 118%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

4-Ethynyl-1-(4-methoxybenzyl)-1H-pyrazole (0.068 g, 0.32 mmol) was added to a solution of tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.10 g, 0.16 mmol), Cu(I)I (0.0015 g, 0.008 mmol), PdCl2(PPh3)2 (0.0056 g, 0.008 mmol) and TEA (0.11 ml, 0.80 mmol) in THF (10 mL) and stirred at 40° C. for 18 hours. Water (10 mL) and ethyl acetate (20 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue obtained was purified by flash chromatography (hexane:ethyl acetate=5:1) to give 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 (0.134 g, 95%) as a solid. LCMS (APCI+) m/z 710 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe residue obtained
  6. customwas purified by flash chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-378c44584fa34ee49682e880f9736b78
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372842B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes