Water → HCID 67431500, compound

HRID 2036618Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([F:19])[CH:18]=1)[NH2:15].C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(N(C)C)=O.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]>[F:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:16]=[C:17]([F:19])[CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a degassed solution of 2-chloro-3-nitro-pyridine (2.7 g, 17.03 mmol) and 3,5-difluoro aniline (2.0 g, 15.5 mmol) in dimethylacetamide (50 mL) was added cesium carbonate (10 g, 30.98 mmol) and was further degassed with nitrogen for 10 min. To the mixture was added xanthophos (448 mg, 0.77 mmol) and Pd2 (dba)3 (851 mg, 0.92 mmol) and stirred at 100° C. for 16 h. After completion of the reaction, water (100 mL) was added and the mixture extracted with EtOAc (500 mL). The organic phase was dried over sodium sulfate and concentrated to provide the crude material, which was purified by column chromatography using 0-5% EtOAc in hexane to yield N-(3,5-difluorophenyl)-3-nitro-pyridin-2-amine: LC-MS (ESI) m/z 250.1 [M−H]−.

Workup

customwas further degassed with nitrogen for 10 min
additionwas added
extractionthe mixture extracted with EtOAc (500 mL)
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated
customto provide the crude material, which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-b62abdb77b884bdf99f24f19c9b7b469
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575183B2

Reaction notes

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