tert-butyl 4-(5-cyclopropyl-3-ethynyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate → tert-butyl 4-(5-cyclopropyl-3-ethyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387535Notes

Reaction equation

HRID 387535 reaction equation
[CH:1]1([C:4]2[C:5]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[C:6]3[C:12]([C:13]#[CH:14])=[N:11][N:10]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([C:4]2[C:5]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:26][CH2:25]3)=[C:6]3[C:12]([CH2:13][CH3:14])=[N:11][N:10]([CH2:15][C:16]4[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86647261tert-butyl 4-(5-cyclopropyl-3-ethynyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 68768039tert-butyl 4-(5-cyclopropyl-3-ethyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylateYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 4-(5-cyclopropyl-3-ethynyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (200 mg, 0.4 mmol) was placed in MeOH (2 mL). Pd/C (175 mg, 0.08 mmol) was then added, and the reaction was stirred at room temperature for 1 hour. The reaction was then filtered and concentrated to give tert-butyl 4-(5-cyclopropyl-3-ethyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (150 mg, 74% yield).

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-294539d0da39484e944ba6a1c508a543
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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