4-Bromo-6-(trifluoromethyl)-1H-indazole → methyl 3-fluoro-4-(6-(trifluoromethyl)-1H-indazol-4-yl)benzoate

HRID 58064

반응식

HRID 58064 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.[F:15][C:16]1[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=1B(O)O>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]>[F:15][C:16]1[CH:21]=[C:20]([CH:19]=[CH:18][C:17]=1[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)[C:22]([O:24][CH3:25])=[O:23]

참가 물질

6

반응물 2

HCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazoleHCID 248243452-Fluoro-4-(methoxycarbonyl)benzeneboronic acid

생성물 1

HCID 89783142methyl 3-fluoro-4-(6-(trifluoromethyl)-1H-indazol-4-yl)benzoate

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

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.402 g, 1.515 mmol), (2-fluoro-4-(methoxycarbonyl)phenyl)boronic acid (0.3 g, 1.515 mmol) and PdCl2(dppf) (0.055 g, 0.076 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light yellow suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated. The crude residue was diluted with EtOAc and washed with water, dried over Na2SO4, and the volatiles were removed via rotary evaporation to give the title compound, which was used without further purification (0.4 g, 78%). ESI-MS m/z [M+H]+ calc'd for C16H10F4N2O2, 339.1. found 339.1.

후처리

  1. concentrationThe reaction mixture was subsequently concentrated
  2. additionThe crude residue was diluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customthe volatiles were removed via rotary evaporation

출처 및 근거

ORD 기록
ord-d3a1dd7dfe19445db35b6d513b26417e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434743B2

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