Cesium carbonate → 3-(6-methoxy-5-nitropyridin-3-yl)-N,N-dimethylprop-2-yn-1-amine

HRID 2388003Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19]([N:22]([CH3:24])[CH3:23])[C:20]#[CH:21]>CN(C=O)C.CC#N.CC#N.Cl[Pd]Cl>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([C:21]#[C:20][CH2:19][N:22]([CH3:24])[CH3:23])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-bromo-2-methoxy-3-nitropyridine (1.50 g, 6.44 mmol) in DMF (30 mL) were added bis(acetonitrile)palladium (II) chloride (83.5 mg, 0.322 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-1-propyl-1-1′-biphenyl (399 mg, 0.837 mmol), cesium carbonate (4.19 g, 12.9 mmol) and propargyl(dimethylamine) (0.832 mL, 7.72 mmol). The reaction mixture was flushed with nitrogen gas and allowed to stir for 4 h at 50° C. The reaction mixture was diluted with EtOAc and washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(6-methoxy-5-nitropyridin-3-yl)-N,N-dimethylprop-2-yn-1-amine (0.41 g, 27%) as a white solid. LCMS (FA): Rt=0.85 min, m/z=236.2 (M+H).

Workup

customThe reaction mixture was flushed with nitrogen gas
additionThe reaction mixture was diluted with EtOAc
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-bc1a6e61857a42648e545980dcbb881b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268992B2

Reaction notes

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