4-Bromo-6-(trifluoromethyl)-1H-indazole → methyl 2-(4-methoxy-3-(6-(trifluoromethyl)-1H-indazol-4-yl)phenyl)acetate

HRID 58063

반응식

HRID 58063 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.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1>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]>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:21][C:22]=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

참가 물질

6

반응물 2

HCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazoleHCID 57576289Methyl 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetate

생성물 1

HCID 89782890methyl 2-(4-methoxy-3-(6-(trifluoromethyl)-1H-indazol-4-yl)phenyl)acetate수율 79%

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 (0.433 g, 1.633 mmol), methyl 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (0.5 g, 1.633 mmol) and PdCl2(dppf) (0.060 g, 0.082 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light brown suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated. The crude residue was dissolved in EtOAc and was washed with water and brine, concentrated, and purified by CombiFlash® chromatography (0-35% MeOH in DCM). The product-containing fractions were combined and concentrated by rotary evaporation to give the title compound (0.47 g, 79%). ESI-MS m/z [M+H]+ calc'd for C18H15F3N2O3, 365.1. found 365.2.

후처리

  1. concentrationThe reaction mixture was subsequently concentrated
  2. dissolutionThe crude residue was dissolved in EtOAc
  3. washwas washed with water and brine
  4. concentrationconcentrated
  5. custompurified by CombiFlash® chromatography (0-35% MeOH in DCM)
  6. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-edf0eb21465345309be40b2e3200d4f8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434743B2

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