Potassium Carbonate → N-[4-(2-tert-butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide

HRID 1042927ノート

反応式

HRID 1042927 の反応式
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[C:29]1[CH:34]=[CH:33][N:32]=[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH:30]=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:36]([O:35][C:31]1[CH:30]=[C:29]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][NH:6][C:4](=[O:5])[C:3]3[C:2]([Cl:1])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:21])=[CH:9][CH:10]=2)[CH:34]=[CH:33][N:32]=1)([CH3:39])([CH3:37])[CH3:38]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 457878724-Bromo-2-tert-butoxypyridineHCID 711499724-[(2,6-Dichloro-benzoylamino)methyl]phenylboronic acid

生成物 1

HCID 71149992N-[4-(2-tert-butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

実験手順

4-[(2,6-Dichloro-benzoylamino)methyl]phenylboronic acid (5 g, 15.4 mmol), potassium carbonate (5 g), and [1,1′bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.56 g, 0.77 mmol) were combined in a round bottom flask. 4-Bromo-2-(t-butoxy)pyridine (3.55 g, 15.4 mmol) was dissolved in 20 mL DMF and added to the flask under stirring. The flask was flushed with nitrogen and 10 mL water was added. The reaction mixture was stirred at 70° C. for two hours. After cooling the mixture was poured into 300 mL ethyl acetate and washed with water and brine. The organic phase was dried with magnesium sulfate and evaporated under vacuum. The crude N-[4-(2-tert-butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide was further purified by silica gel chromatography (eluent: hexone/ethyl acetate 1:1).

後処理

  1. additionadded to the flask
  2. customThe flask was flushed with nitrogen and 10 mL water
  3. additionwas added
  4. stirringThe reaction mixture was stirred at 70° C. for two hours
  5. temperatureAfter cooling the mixture
  6. additionwas poured into 300 mL ethyl acetate
  7. washwashed with water and brine
  8. dry with materialThe organic phase was dried with magnesium sulfate
  9. customevaporated under vacuum
  10. customThe crude N-[4-(2-tert-butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide was further purified by silica gel chromatography (eluent: hexone/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-07ce29d136a6489fa0140dadfffe5465
出典データセット
uspto-grants-2013_10
特許番号
US08558001B2

反応ノート

読み込み中…