Cesium carbonate → HCID 70665111, compound

HRID 1403319Notes

Reaction equation

HRID 1403319 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:16]1[C:25]([N:26]([CH:28]([CH3:30])[CH3:29])[CH3:27])=[N:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:31]([O-:33])=[O:32])[CH:22]=2)[N:17]=1.[C:34]([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].Cl[Cu]>[CH:28]([N:26]([CH3:27])[C:25]1[C:16]([C:9]2[CH:10]=[N:11][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:7][CH:8]=2)=[N:17][C:18]2[C:23]([N:24]=1)=[CH:22][C:21]([C:31]([O:33][CH3:34])=[O:32])=[CH:20][CH:19]=2)([CH3:30])[CH3:29]

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 46737701[6-(Pyrrolidin-1-yl)pyridin-3-yl]boronic acidHCID 86670555HCID 86670555, compound

Product 1

HCID 70665111HCID 70665111, compoundYield 55.3%

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-(pyrrolidin-1-yl)pyridin-3-ylboronic acid (244.9 mg, 1.28 mmol) in N,N-dimethylformamide (6 mL) was added 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (170.0 mg, 0.58 mmol), Pd(OAc)2 (17.2 mg, 0.03 mmol), DPPF (28.3 mg, 0.05 mmol), CuCl (50.5 mg, 0.51 mmol) and Cs2CO3 (332.4 mg, 1.02 mmol) with stirring for 0.5 h at 100° C. with an inert atmosphere of nitrogen. The reaction mixture was cooled and extracted with ethyl acetate (3×80 mL), dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 2.5% ethyl acetate in petroleum ether to afford methyl 3-(isopropyl(methyl)amino)-2-(6-(pyrrolidin-1-yl)pyridin-3-yl)quinoxaline-6-carboxylate as a light yellow solid (130.0 mg, 55%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (3×80 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by a silica gel column with 2.5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-c1106dc9f9c94af9987eeab5f02cea5b
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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