Potassium Carbonate → N-(4-fluoro-3-nitrophenyl)-3-(pyrimidin-4-yl)pyridin-2-amine

HRID 1361660Notes

Reaction equation

HRID 1361660 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].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.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:2]2[C:7]([C:8]3[CH:13]=[CH:12][N:11]=[CH:10][N:9]=3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 677684-Fluoro-3-nitroanilineHCID 634876Binap, (A+-)-HCID 161089744-(2-Chloropyridin-3-yl)pyrimidine

Product 1

HCID 66970524N-(4-fluoro-3-nitrophenyl)-3-(pyrimidin-4-yl)pyridin-2-amine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-(2-Chloro-pyridin-3-yl)-pyrimidine (60 mg, 0.30 mmol), 4-fluoro-3-nitrobenzenamine (56 mg, 0.36 mmol), Pd(OAc)2 (4 mg, 0.012 mmol), rac-BINAP (8 mg, 0.012 mmol) and K2CO3 (829 mg, 6.0 mmol) in toluene (3.0 mL) were reacted overnight at 130° C. The reaction was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filter, concentrated and purified by silica gel chromatography (0-100% EtOAc/hexanes) yielding the title compound. MS m/z=312 [M+1]+. Calc'd for C15H10FN5O2: 311.28.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfilter
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-36ac806058524600b276656acdf2560a
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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