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

HRID 509529노트

반응식

HRID 509529 반응식
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]

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 24290Palladium Chloride촉매HCID 962Water용매2회HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b69134e638e0459bae38e193d81665d5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096584B2

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