1,10-Phenanthroline → HCID 67089136, compound

HRID 1943945Notes

Reaction equation

HRID 1943945 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:3]=1.[CH:23]1([CH2:27][OH:28])[CH2:26][CH2:25][CH2:24]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>CCOC(C)=O.[Cu]I>[CH:23]1([CH2:27][O:28][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=3)[N:4]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:3]=2)[CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 78130CyclobutylcarbinolHCID 67088863HCID 67088863, compound

Product 1

HCID 67089136HCID 67089136, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

3-Iodo-1-(4-methoxybenzyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (0.100 g, 0.244 mmol), cyclobutylmethanol (1.05 mL, 12.19 mmol), 1,10-phenanthroline (0.044 g, 0.244 mmol), copper (I) iodide (0.046 g, 0.244 mmol), and 40% KF/Al2O3 (0.248 g, 1.71 mmol) were combined in a reaction vial and heated to 115° C. for 24 hours. After cooling to room temperature, the mixture was diluted with EtOAc (20 mL) and filtered through GF/F filter paper. The filtrate was then concentrated and passed through a 10 g SepPak cartridge, eluting with DCM. The fractions were collected and then purified by preparative TLC (2×0.5 mm plates, 15% EtOAc/hexanes) to give 3-(cyclobutylmethoxy)-1-(4-methoxybenzyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (22 mg, 24.5%) as a solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered through GF/F
  3. filtrationfilter paper
  4. concentrationThe filtrate was then concentrated
  5. washeluting with DCM
  6. customThe fractions were collected
  7. custompurified by preparative TLC (2×0.5 mm plates, 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9a2680492a6146c18d662631beb29396
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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