Aniline → [4-(5-Methyl-3-phenyl-isoxazol-4-yl)-pyridin-2-yl]phenyl-amine

HRID 2120866Notes

Reaction equation

HRID 2120866 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][O:11][C:12]=2[CH3:13])[CH:5]=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.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.CC([O-])(C)C.[Na+]>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].CCOC(C)=O.C(Cl)Cl>[CH3:13][C:12]1[O:11][N:10]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]=1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 634876Binap, (A+-)-HCID 234356652-Bromo-4-(5-methyl-3-phenyl-isoxazol-4-yl)-pyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 69143504[4-(5-Methyl-3-phenyl-isoxazol-4-yl)-pyridin-2-yl]phenyl-amineYield 61.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of the above Compound 17a (20 mg, 0.063 mmol), aniline (7.0 μL, 0.076 mmol) and BINAP (5.6 mg, 0.009 mmol) in toluene (0.6 mL) at 25° C. was added Pd2(dba)3 (2.7 mg, 0.003 mmol) followed by NaOtBu (9.1 mg, 0.095 mmol). The solution was heated to 80° C. for 2 h. The solution was cooled, filtered and concentrated. Preparative thin layer chromatography (SiO2, 5% EtOAc/CH2Cl2) provided the title compound (12.6 mg, 0.0385 mmol, 61%).

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-86ef34d1e45443c989ae912eaa7881ac
Source dataset
uspto-grants-2004_02
Patent number
US06693108B2

Reaction notes

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