Sodium Carbonate → 1,2-Dihydro-2-(4-trifluoromethylphenyl)-6-(3-trifluoromethyl-2-pyridinyl)-1-(2-(trimethylsilyl)ethoxymethyl)-3H-indazol-3-one

HRID 270685노트

반응식

HRID 270685 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:29])[N:7]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.CC([O-])=O.[K+].Cl[C:54]1[C:59]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:57]=[CH:56][N:55]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1(P([Pd-3](Cl)(Cl)(P(C2C=CC=CC=2)C2C=CC=CC=2)[C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[F:28][C:25]([F:27])([F:26])[C:22]1[CH:23]=[CH:24][C:19]([N:7]2[C:6](=[O:29])[C:5]3[C:9](=[CH:10][C:2]([C:54]4[C:59]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:57]=[CH:56][N:55]=4)=[CH:3][CH:4]=3)[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])=[CH:20][CH:21]=1

참가 물질

8

반응물 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 2733548Bis(pinacolato)diboraneHCID 692032346-Bromo-1,2-dihydro-2-(4-trifluoromethylphenyl)-1-(2-trimethylsilyl ethoxymethyl)-3H-indazol-3-one

생성물 1

HCID 866128481,2-Dihydro-2-(4-trifluoromethylphenyl)-6-(3-trifluoromethyl-2-pyridinyl)-1-(2-(trimethylsilyl)ethoxymethyl)-3H-indazol-3-one수율 13.9%

시약·촉매·용매 2

HCID 178479788HCID 178479788, 화합물촉매2회HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

The product of Step 5 (1.3 g, 2.6 mmol), was dissolved in dioxane (10 mL) and flushed with N2. Bis(pinacolato)diboron (680 mg, 2.6 mmol), bis(diphenylphosphino)ferrocenyl palladium(II) dichloride (60 mg) and KOAc (380 mg, 3.9 mmol) were added. The mixture was stirred at 100° C. overnight. 2-Chloro-3-trifluoromethylpyridine (470 mg, 2.6 mmol), bis(diphenylphosphino)ferrocenyl palladium(II) dichloride (20 mg) and saturated Na2CO3 solution (1 mL) were added, and the mixture heated at reflux for a further 18 h. Purification by column chromatography gave 0.2 g of product as an oil.

후처리

  1. customflushed with N2
  2. temperaturethe mixture heated
  3. temperatureat reflux for a further 18 h
  4. customPurification by column chromatography

출처 및 근거

ORD 기록
ord-966c5ef759ed41eaadad4c4e9772a7c0
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449585B2

반응 노트

불러오는 중…