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

HRID 2038343노트

반응식

HRID 2038343 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0c1678236be54a26ad856dd0e8afc2c1
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575353B2

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