[4-(Methoxycarbonyl)-2-methylphenyl]boronic acid → HCID 89782937, 화합물

HRID 58065

반응식

HRID 58065 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]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[C:21]([CH3:28])[CH:20]=1)=[O:18]>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]>[CH3:28][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][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)[C:17]([O:16][CH3:15])=[O:18]

참가 물질

6

반응물 2

HCID 22171419[4-(Methoxycarbonyl)-2-methylphenyl]boronic acidHCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazole

생성물 1

HCID 89782937HCID 89782937, 화합물

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

To a microwave vial was added a mixture 4-bromo-6-(trifluoromethyl)-1H-indazole (0.478 g, 1.804 mmol), (4-(methoxycarbonyl)-2-methylphenyl)boronic acid (0.35 g, 1.804 mmol) and PdCl2(dppf) (0.066 g, 0.090 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light yellow suspension was heated at 140° C. for 60 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the residue was diluted with EtOAc and washed with water. The volatiles were removed via rotary evaporation to give the title compound, which was used without further purification (0.53 g). ESI-MS m/z [M+H]+ calc'd for C17H13F3N2O2, 335.1. found 335.2.

후처리

  1. concentrationThe reaction mixture was subsequently concentrated
  2. additionthe residue was diluted with EtOAc
  3. washwashed with water
  4. customThe volatiles were removed via rotary evaporation

출처 및 근거

ORD 기록
ord-baa272f5ec214d7b956cc5f094773292
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434743B2

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