1,10-Phenanthroline → tert-butyl 4-(3-(2-tert-butoxyethoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387571Notes

Reaction equation

HRID 387571 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[N:4]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[N:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:47]([O:51][CH2:52][CH2:53][OH:54])([CH3:50])([CH3:49])[CH3:48].[F-].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:47]([O:51][CH2:52][CH2:53][O:54][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[N:4]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[N:3]=1)([CH3:50])([CH3:49])[CH3:48]

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 242322-(Tert-butoxy)ethan-1-olHCID 522689Potassium FluorideHCID 68759242tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 68755474tert-butyl 4-(3-(2-tert-butoxyethoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.12 g, 0.218 mmol), Cu(I)I (0.0416 g, 0.218 mmol), 1,10-phenanthroline (0.0394 g, 0.218 mmol), 2-tert-butoxyethanol (0.774 g, 6.55 mmol) and KF on Al2O3 (40%; 0.222 g, 1.53 mmol) in toluene (4 mL) were stirred at 120° C. for 40 hours. The reaction was then cooled to room temperature. Ethyl acetate (10 mL) was then added. The reaction was filtered through a pad of celite and concentrated to dryness. The resulting residue was purified by chromatography (hexane:ethyl acetate, 3:1) to give tert-butyl 4-(3-(2-tert-butoxyethoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.080 g, 68%) as a solid. MS APCI (+) m/z 540.5 detected.

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. concentrationconcentrated to dryness
  3. customThe resulting residue was purified by chromatography (hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-5b84431b310c42098a70b7f9f8d3f991
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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