Cesium carbonate → 1-(4-(6-Nitropyridin-3-YL)piperazin-1-YL)ethan-1-one

HRID 2189271Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[C:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:13])[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:17]2[CH2:18][CH2:19][N:14]([C:11](=[O:13])[CH3:12])[CH2:15][CH2:16]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 5-bromo-2-nitropyridine (406 mg, 2 mmol) and 1-acetylpiperazine (256 mg, 2 mmol) in toluene (5 mL) is added Cs2CO3, then Pd2(dba)3 (74 mg, 0.08 mmol) and BINAP (100 mg, 0.16 mmol) are added. The mixture is degassed, and heated at 100° C. for 16 hours. Then the mixture is cooled down to room temperature, diluted with EtOAc, and filtered through celite. The filtrate is concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=0.7:99.3 to 6:93) to give 270 mg of the title compound as yellow solid.

Workup

customThe mixture is degassed
temperatureThen the mixture is cooled down to room temperature
additiondiluted with EtOAc
filtrationfiltered through celite
concentrationThe filtrate is concentrated under reduced pressure
customThe crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=0.7:99.3 to 6:93)

Sources & evidence

ORD record: ord-f6e4a121a91e43aea060ec5808bd5e65
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324225B2

Reaction notes

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