Sodium Carbonate → (2Benzo[1,2,5]oxadiazol-5-yl-phenyl)-dimethyl-amine

HRID 1867507ノート

反応式

HRID 1867507 の反応式
C([O-])(=O)C.[K+].Br[C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:15]=1)=[N:12][O:13][N:14]=2.C(=O)([O-])[O-].[Na+].[Na+].Br[C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[N:25]([CH3:27])[CH3:26]>CN(C=O)C.O>[N:14]1[O:13][N:12]=[C:11]2[CH:15]=[C:7]([C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[N:25]([CH3:27])[CH3:26])[CH:8]=[CH:9][C:10]=12

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 1365272-Bromo-N,N-dimethylanilineHCID 517044Potassium AcetateHCID 27762985-Bromo-2,1,3-benzoxadiazole

生成物 1

HCID 68878349(2Benzo[1,2,5]oxadiazol-5-yl-phenyl)-dimethyl-amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

523 mg (1.65 eq.) bis(pinacolato)diboran, 552 mg (4.5 eq.) potassium acetate and 51 mg (0.01 eq.) PdCl(dppf)-CH2Cl2 are added to a solution of 373 mg 5-bromo-benzo[1,2,5]oxadiazole in 8 mL DMF and heated to 80° C. under continuous stirring for 6 hours. 662 mg (5 eq.) sodium carbonate in 3.3 mL water are added together with 500 mg (1 eq.) 2-bromo-N,N-dimethylaniline and 51 mg (0.01 eq.) PdCl(dppf)-CH2Cl2 to the reaction mixture, which is stirred for another 18 hours at 80° C., cooled to room temperature and extracted with ethyl acetate and water. The combined organic phases are washed with brine, dried over magnesium sulfate and evaporated. The residue is column chromatographed (hexane, then hexane/ethyl acetate 8:1) to yield the desired product as an orange resin. MS(ES+): 240 (M+1).

後処理

  1. stirringis stirred for another 18 hours at 80° C.
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate and water
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customchromatographed (hexane

出典と根拠

ORDレコード
ord-84c49cd67ec942568ab3dc4c0b137042
出典データセット
uspto-grants-2009_12
特許番号
US07632851B2

反応ノート

読み込み中…