1,10-Phenanthroline → HCID 90031146, compound

HRID 624652Notes

Reaction equation

HRID 624652 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.[N:14]1[CH:19]=[C:18](B(O)O)[CH:17]=[N:16][CH:15]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[N:14]1[CH:19]=[C:18]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]2)[CH:17]=[N:16][CH:15]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 8471TriethylamineHCID 589098Methyl indole-3-carboxylateHCID 2795193(Pyrimidin-5-yl)boronic acid

Product 1

HCID 90031146HCID 90031146, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a vial containing methyl 1H-indole-3-carboxylate (471 mg, 2.69 mmol), pyrimidin-5-ylboronic acid (1.0 g, 8.07 mmol), copper (II) acetate (635 mg, 3.5 mmol), 4 {acute over (Å)} molecular sieves (4 g) and 1,10-phenanthroline (970 mg, 5.38 mmol) were added DCM (10.7 ml) and triethylamine (0.375 ml, 2.69 mmol). The mixture was stirred at RT for 7 days then filtered through a pad of Celite (washed with MeOH). Evaporation and purification by HPLC (after dilution with DMF and filtration) afforded the title compound as a tan solid.

Workup

  1. filtrationthen filtered through a pad of Celite (washed with MeOH)
  2. customEvaporation and purification
  3. filtrationby HPLC (after dilution with DMF and filtration)

Sources & evidence

ORD record
ord-4c3504c1e3074c23b0d85a7ce8c8b188
Source dataset
uspto-grants-2016_04
Patent number
US09303045B2

Reaction notes

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