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

HRID 509529ノート

反応式

HRID 509529 の反応式
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]

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24290Palladium Chloride触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b69134e638e0459bae38e193d81665d5
出典データセット
uspto-grants-2015_08
特許番号
US09096584B2

反応ノート

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