Potassium Carbonate → 5-(4-(Methylsulfonyl)phenyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-amine

HRID 509529Notes

Reaction equation

HRID 509529 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]2[O:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:26][N:27]=2)[C:5]([N:8](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[N:6][CH:7]=1.[CH3:34][S:35]([C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1)(=[O:37])=[O:36].C(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C(Cl)Cl.Cl[Pd]Cl>[CH3:34][S:35]([C:38]1[CH:43]=[CH:42][C:41]([C:2]2[CH:3]=[C:4]([C:23]3[O:24][C:25]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[N:26][N:27]=3)[C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:40][CH:39]=1)(=[O:37])=[O:36]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 11714598(4-(N,N-Dimethylamino)phenyl)di-tert-butyl phosphineHCID 67481749tert-Butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate

Product 1

HCID 546731975-(4-(Methylsulfonyl)phenyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-amine

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (250 mg, 0.4832 mmol), (4-methylsulfonylphenyl)boronic acid (116.0 mg, 0.5798 mmol), 4-ditert-butylphosphanyl-N,N-dimethyl-aniline; dichloropalladium (3.421 mg, 0.004832 mmol) and K2CO3 (133.6 mg, 0.9664 mmol) in Toluene (2.250 mL) and water (250.0 μL) was heated to 100° C. for 48 hours. The mixture was allowed to cool to ambient temperature and diluted with DCM and water. The organic layer was separated, washed with 1M NaOH solution, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was triturated with DCM to give the desired product as a peach solid (70 mg, 37% Yield). 1H NMR (400.0 MHz, DMSO) δ 3.27 (s, 3H), 7.64-7.69 (m, 5H), 8.01 (d, J=8.5 Hz, 2H), 8.07 (d, J=8.6 Hz, 2H), 8.25-8.27 (m, 2H), 8.66 (d, J=2.5 Hz, 1H) and 8.72 (d, J=2.5 Hz, 1H) ppm; MS (ES+) 392.9.

Workup

  1. customThe organic layer was separated
  2. washwashed with 1M NaOH solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was triturated with DCM

Sources & evidence

ORD record
ord-b69134e638e0459bae38e193d81665d5
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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