4-Bromo-6-(trifluoromethyl)-1H-indazole → 4-(6-chloro-2-methylpyridin-3-yl)-6-(trifluoromethyl)-1H-indazole

HRID 58111노트

반응식

HRID 58111 반응식
Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[Cl:15][C:16]1[N:21]=[C:20]([CH3:22])[C:19](B(O)O)=[CH:18][CH:17]=1>O1CCOCC1.C([O-])(O)=O.[Na+].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:15][C:16]1[N:21]=[C:20]([CH3:22])[C:19]([C:2]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]3[C:3]=2[CH:4]=[N:5][NH:6]3)=[CH:18][CH:17]=1

참가 물질

6

반응물 2

HCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazoleHCID 441191526-Chloro-2-methylpyridine-3-boronic acid

생성물 1

HCID 897832784-(6-chloro-2-methylpyridin-3-yl)-6-(trifluoromethyl)-1H-indazole수율 605.6%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
140 °C

실험 절차

The reaction was carried out in eight microwave vials. To each vial were added 4-bromo-6-(trifluoromethyl)-1H-indazole (0.5 g, 1.886 mmol), (6-chloro-2-methylpyridin-3-yl)boronic acid (0.3875 g, 2.264 mmol) and PdCl2(dppf) (0.069 g, 0.0944 mmol) in dioxane (12 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light-brown suspensions were each heated at 140° C. for 60 minutes in a microwave reactor. The reaction mixtures were combined and concentrated and the crude residue was diluted with EtOAc and washed with water. The volatiles were removed via rotary evaporation and the product purified by CombiFlash® chromatography, eluting with a gradient of 0-100% EtOAc in heptane over a period of 180 minutes. The product-containing fractions were combined and the volatiles removed via rotary evaporation to give the title compound (3.56 g, 76%). ESI-MS m/z [M+H]+ calc'd for C14H9ClF3N3, 312.05. found 311.89.

후처리

  1. customThe reaction mixtures
  2. concentrationconcentrated
  3. additionthe crude residue was diluted with EtOAc
  4. washwashed with water
  5. customThe volatiles were removed via rotary evaporation
  6. customthe product purified by CombiFlash® chromatography
  7. washeluting with a gradient of 0-100% EtOAc in heptane over a period of 180 minutes
  8. customthe volatiles removed via rotary evaporation

출처 및 근거

ORD 기록
ord-b2a6bf0f8af745aba8c4ecd316b99fbf
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434743B2

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