1,10-Phenanthroline → HCID 68756103, compound

HRID 387596Notes

Reaction equation

HRID 387596 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[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](CC2C=CC(OC)=CC=2)[N:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[CH3:53][C:54]1([CH3:61])[O:58][C@H:57]([CH2:59][OH:60])[CH2:56][O:55]1.[F-].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:53][C:54]1([CH3:61])[O:58][C@H:57]([CH2:59][O:60][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:9]=3[N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[NH:4][N:3]=2)[CH2:56][O:55]1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 522689Potassium FluorideHCID 736056(R)-SolketalHCID 68760648HCID 68760648, compound

Product 1

HCID 68756103HCID 68756103, compoundYield 114.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.15 g, 0.24 mmol, see Example 9), Cu(I)I (0.046 g, 0.24 mmol), 1,10-phenanthroline (0.043 g, 0.24 mmol), (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol (0.95 g, 7.2 mmol) and KF on Al2O3 (40%; 0.24 g, 1.68 mmol) in toluene (4 mL) was stirred at 110° C. for 60 hours. Ethyl acetate (10 mL) was then added, and the reaction mixture was filtered through a pad of celite. The reaction was then concentrated to dryness, and the residue was purified by column chromatography (hexane:ethyl acetate=1:1) to give (R)-tert-butyl 4-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.14 g, 93%) as a solid. MS APCI (+) m/z 630.2 detected.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite
  2. concentrationThe reaction was then concentrated to dryness
  3. customthe residue was purified by column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-06b99616d2374ceb947c000ff4ce5baf
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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