Acetamide → N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide

HRID 626496

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:18]([NH2:21])(=[O:20])[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>O1CCOCC1.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].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[N+:15]([C:12]1[N:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:21][C:18](=[O:20])[CH3:19])[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A degassed solution of Example A1 (2.0 g, 7.95 mmol) in dioxane (30 mL) added treated with acetamide (1.878 g, 31.8 mmol), Cs2CO3 (2.59 g, 7.95 mmol), X-Phos (0.189 g, 0.397 mmol), and Pd2(dba)3 (0.364 g, 0.397 mmol) and heated at 80° C. for 16 h. The mixture was cooled to RT, treated with EtOAc, the solids removed via filtration through diatomaceous earth and rinsed well with EtOAc. The filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (1.48 g, 68%). MS (ESI) m/z: 275.1 (M+H+).

Workup

temperatureThe mixture was cooled to RT
customthe solids removed via filtration through diatomaceous earth
washrinsed well with EtOAc
washThe filtrate was washed with water
dry with materialbrine, dried over Na2SO4
concentrationconcentrated to dryness
custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record: ord-b3c4a19b1b1e40a3bb8d496342721504
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309224B2

Linked notes

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