Potassium Carbonate → 3-(Chloro-difluoro-methyl)-6-(4-trifluoromethoxy-phenyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 2205746노트

반응식

HRID 2205746 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([Cl:14])([F:13])[F:12])=[N:9][N:10]=2)[CH:7]=1.[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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:14][C:11]([F:13])([F:12])[C:8]1[N:6]2[CH:7]=[C:2]([C:21]3[CH:20]=[CH:19][C:18]([O:17][C:16]([F:15])([F:27])[F:28])=[CH:23][CH:22]=3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 581189096-Bromo-3-(chlorodifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

생성물 1

HCID 581189423-(Chloro-difluoro-methyl)-6-(4-trifluoromethoxy-phenyl)-[1,2,4]triazolo[4,3-a]pyridine

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

6-Bromo-3-(chloro-difluoro-methyl)-[1,2,4]triazolo[4,3-a]pyridine (2.76 g, 9.8 mmol), 4-trifluoromethoxyphenyl boronic acid (2.5 g, 12.1 mmol), dppfPdCl2 (1,1′-bis(diphenylphosphino)ferrocene palladium dichloride) (350 mg, 0.5 mmol), and potassium carbonate (2.76 g, 20 mmol) were suspended in degassed toluene (20 mL), degassed isopropanol (10 mL) and degassed water (10 mL) under an atmosphere of nitrogen. The reaction mixture was heated at 70° C. for 1 hour before being cooled to room temperature. The aqueous phase was discarded and the organic phase was concentrated and purified by flash chromatography (rf=0.5 in 1:1 hexanes/ethyl acetate) to give 3-(chloro-difluoro-methyl)-6-(4-trifluoromethoxy-phenyl)[1,2,4]triazolo[4,3-a]pyridine as a pale orange powder.

후처리

  1. customdegassed isopropanol (10 mL)
  2. customdegassed water (10 mL) under an atmosphere of nitrogen
  3. temperaturebefore being cooled to room temperature
  4. concentrationthe organic phase was concentrated
  5. custompurified by flash chromatography (rf=0.5 in 1:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-70554b3b9d3b478a8fe537d12912d3fb
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371329B2

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