Sodium Carbonate → 2-Chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amine

HRID 405243

반응식

HRID 405243 반응식
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O.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]>[Cl:9][C:3]1[CH:4]=[C:5]([NH2:6])[CH:7]=[CH:8][C:2]=1[C:15]1[CH:16]=[CH:17][C:12]([C:11]([F:22])([F:21])[F:10])=[CH:13][CH:14]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 888884-Bromo-3-chloroanilineHCID 27343894-(Trifluoromethyl)phenylboronic acid

생성물 1

HCID 688342842-Chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amine

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

4-bromo-3-chloroaniline (2.1 g, 10.2 mmol), (4-(trifluoromethyl)phenyl)boronic acid (2.7 g, 14.2 mmol), Pd(dppf)Cl2 (744 mg, 1.0 mmol), 2M aqueous Na2CO3 (15.3 mL, 30.5 mmol) were dissolved in 1,4-dioxane (30 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, was diluted with EtOAc, washed with water and brine. The organic layer was dried (Na2SO4), concentrated and diethyl ether was added. The resulting precipitate was filtered and dried in vacuo to yield the title compound.

후처리

  1. temperatureAfter 16 h the resulting mixture was cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. additiondiethyl ether was added
  6. filtrationThe resulting precipitate was filtered
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-d72259e8bf7c48729e74a335ef3854e4
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748624B2

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