Potassium Carbonate → N-(1-{4'-[3-Methyl-4-(6-phenyl-pyridin-2-ylamino)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarbonyl)-methanesulfonamide

HRID 1624519Notes

Reaction equation

HRID 1624519 reaction equation
[NH2:1][C:2]1[C:3]([CH3:29])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3([C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[O:23])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.Br[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:32]=1.C(=O)([O-])[O-].[K+].[K+].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>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:29][C:3]1[C:2]([NH:1][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:32]=2)=[C:6]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]4([C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[O:23])[CH2:21][CH2:20]4)=[CH:17][CH:18]=3)=[CH:11][CH:12]=2)[O:5][N:4]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 5686792-Bromo-6-phenylpyridineHCID 634876Binap, (A+-)-HCID 66577832N-{1-[4'-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarbonyl}-methanesulfonamide

Product 1

HCID 51347416N-(1-{4'-[3-Methyl-4-(6-phenyl-pyridin-2-ylamino)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarbonyl)-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

N-{1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarbonyl}-methanesulfonamide (0.103 g, 0.25 mmol), 2-bromo-6-phenylpyridine (0.059 g, 0.25 mmol), potassium carbonate (0.243 g, 0.75 mmol), and BINAP (15 mg, 0.025 mmol) were combined in THF (10 mL) and the solution was degassed with N2 for 10 minutes. Palladium(II)acetate (0.003 g, 0.0125 mmol) was added and degassing was continued for 10 minutes. The reaction mixture was sealed and heated at 65° C. overnight then poured into EtOAc/water. The organic layer was concentrated and purified by silica gel chromatography to give the title compound.

Workup

  1. customthe solution was degassed with N2 for 10 minutes
  2. customdegassing
  3. customThe reaction mixture was sealed
  4. additionthen poured into EtOAc/water
  5. concentrationThe organic layer was concentrated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3ef1e5e941fb473b802f8a6eecee55c1
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

Loading…