Sodium Carbonate → HCID 22617308, 화합물

HRID 841847노트

반응식

HRID 841847 반응식
[CH2:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22](OS(C(F)(F)F)(=O)=O)=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH3:2].OB(O)[C:35]1[CH:40]=[C:39]([F:41])[C:38]([O:42][C:43]([F:46])([F:45])[F:44])=[C:37]([F:47])[CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].O>[CH2:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:35]4[CH:40]=[C:39]([F:41])[C:38]([O:42][C:43]([F:46])([F:45])[F:44])=[C:37]([F:47])[CH:36]=4)=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH3:2]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 23443787B-[3,5-Difluoro-4-(trifluoromethoxy)phenyl]boronic acidHCID 54072023HCID 54072023, 화합물

생성물 1

HCID 22617308HCID 22617308, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 962Water용매

실험 절차

6.3 g (13 mmol) of 4-(2-(4-(4-ethoxymethylcyclohexyl) cyclohexyl) ethyl) trifluoromethylsulfonyloxybenzene, 4.2 g (17 mmol) of dihydroxy (3,5-difluoro-4-trifluoromethoxyphenyl) borane, 5% palladium on activated charcoal (1.0 g) and 5.7 g (54 mmol) of sodium carbonate were refluxed in toluene/alcohol/water (1/1/1 v/v, 80 ml) under a nitrogen atmosphere for 3 days. After cooling, the reaction solution was added with water (150 ml) and extracted twice with toluene (150 ml). An organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent therein was distilled off under a reduced pressure. The residue thus obtained was purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol) to obtain colorless crystals of 4-(4-(2-(4-(4-ethoxymethylcyclohexyl)cyclohexyl)ethyl)phenyl)-2,6-difluorotrifluoromethoxybenzene.

후처리

  1. temperatureAfter cooling
  2. extractionextracted twice with toluene (150 ml)
  3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent therein was distilled off under a reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol)

출처 및 근거

ORD 기록
ord-c1b6d4f3fe404ff78aa7c7a1464c192a
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372153B1

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