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

HRID 387534Notes

Reaction equation

HRID 387534 reaction equation
[CH:1]1([C:4]2[C:5]([N:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[C:6]3[C:12]([C:13]#[C:14][Si](C)(C)C)=[N:11][N:10]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH:1]1([C:4]2[C:5]([N:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[C:6]3[C:12]([C:13]#[CH:14])=[N:11][N:10]([CH2:19][C:20]4[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 68769357tert-butyl 4-(5-cyclopropyl-1-(4-methoxybenzyl)-3-((trimethylsilyl)ethynyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 86647261tert-butyl 4-(5-cyclopropyl-3-ethynyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylateYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(5-cyclopropyl-1-(4-methoxybenzyl)-3-((trimethylsilyl)ethynyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (280 mg, 0.50 mmol) was placed in THF (8 mL) at 0° C. TBAF (0.54 mL, 0.54 mmol) was then added, and the reaction stirred for 30 minutes at room temperature. The reaction was then poured into saturated Na2CO3, and extracted with DCM. The combined organic fractions were dried, filtered, and concentrated to give the crude product, which was purified by column chromatography to give tert-butyl 4-(5-cyclopropyl-3-ethynyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (250 mg, 96% yield).

Workup

  1. extractionextracted with DCM
  2. customThe combined organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-53bf62f3cdec41a9b025a5d8ace2297f
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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