Pyridine → HCID 70664837, compound

HRID 1403507Notes

Reaction equation

HRID 1403507 reaction equation
[CH3:1][N:2]([CH:22]([CH3:24])[CH3:23])[C:3]1[C:4]([C:17]2[CH:18]=[N:19][NH:20][CH:21]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=2.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N1C=CC=CC=1.CCN(CC)CC>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][N:2]([CH:22]([CH3:24])[CH3:23])[C:3]1[C:4]([C:17]2[CH:21]=[N:20][N:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:18]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=2

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 70664687HCID 70664687, compound

Product 1

HCID 70664837HCID 70664837, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 3-[methyl(propan-2-yl)amino]-2-(1H-pyrazol-4-yl)quinoxaline-6-carboxylate (150 mg, 0.46 mmol) in dioxane (10 mL) was added phenylboronic acid (112 mg, 0.92 mmol), Cu(OAc)2 (123 mg, 0.68 mmol), pyridine (31 mg, 0.39 mmol) and Et3N (310 mg, 2.3 mmol). The resulting solution was stirred for 36 h at room temperature and concentrated under vacuum. The residue was purified via silica gel chromatography (1% to 5% ethyl acetate in petroleum ether) to afford methyl 3-[methyl(propan-2-yl)amino]-2-(1-phenyl-1H-pyrazol-4-yl)quinoxaline-6-carboxylate as a yellow solid (80 mg, 43%).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified via silica gel chromatography (1% to 5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-fb77ec2b48394cda86585d8b64a597f3
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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