1,10-Phenanthroline → HCID 66734284, compound

HRID 1929710Notes

Reaction equation

HRID 1929710 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16](I)=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([CH3:29])[CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:44](=O)([O-])[O-:45].[Cs+].[Cs+]>CO.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16]([O:45][CH3:44])=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([CH3:29])[CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 66734235HCID 66734235, compound

Product 1

HCID 66734284HCID 66734284, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Procedure

A solution of 8-[2-(3,4-dimethyl-phenyl)-ethyl]-3-ethyl-1-iodo-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (1.500 g; 2.944 mmol) in anhydrous MeOH (30 ml) was treated successively with copper(I) iodide (56 mg; 0.294 mmol), 1,10-phenanthroline (116.7 mg; 0.589 mmol), and cesium carbonate (1.535 g; 4.711 mmol). The resulting brown suspension was sealed and put in the microwave oven (150 W; 150° C.; 13 bars; 1h30). The resulting brown suspension was concentrated to dryness under reduced pressure and the crude was purified by FC (EA/heptane: 2/3 to 3/2]. The expected product 8-[2-(3,4-dimethyl-phenyl)-ethyl]-3-ethyl-1-methoxy-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester was obtained as a yellow oil (260.6 mg; 21%). LC-MS: tR=0.91 min.; [M+H]+=414.35 g/mol.

Workup

  1. customThe resulting brown suspension was sealed
  2. customput in the microwave oven (150 W; 150° C.; 13 bars; 1h30)
  3. concentrationThe resulting brown suspension was concentrated to dryness under reduced pressure
  4. customthe crude was purified by FC (EA/heptane

Sources & evidence

ORD record
ord-93ab7a624e6046e99e8eaf18e39277fa
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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