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Ethyl Acetate → HCID 178505686, 화합물

HRID 1512164
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HRID 1512164 반응식
Br[C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]([CH:9]=[CH:10][CH:11]3[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]3)=[N:8][C:4]=2[CH:3]=1.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:23]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(COC)OC.[Pd](Cl)Cl.C(C1C=C[C-](P)C=1C(C)(C)C)(C)(C)C.[CH-]1C=CC=C1.[Fe+2].O>[F:17][C:14]1([F:18])[CH2:15][CH2:16][CH:11]([CH:10]=[CH:9][C:7]2[NH:6][C:5]3[CH:19]=[CH:20][C:2]([C:23]4[C:24]([C:28]([F:30])([F:31])[F:29])=[CH:25][CH:26]=[CH:27][C:22]=4[F:21])=[CH:3][C:4]=3[N:8]=2)[CH2:12][CH2:13]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 162171682-Fluoro-6-(trifluoromethyl)phenylboronic acidHCID 178506001HCID 178506001, 화합물

생성물 1

HCID 178505686HCID 178505686, 화합물

시약·촉매·용매 3

HCID 131729813
Di-t-butyl-phosphinoferrocene palladium chloride
촉매
HCID 962Water용매
HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 5-bromo-2-[2-(4,4-difluoro-cyclohexyl)-vinyl]-1H-benzimidazole (0.030 g, 0.088 mmol, prepared as in STEP F above), 2-fluoro-6-trifluoromethylphenyl boronic acid (0.040 g, 0.19 mmol), 1,1-bis(di-t-butyl-phosphinoferrocene palladium chloride (0.012 g, 0.018 mmol) in dimethoxyethane (2 mL) and 2M sodium carbonate (1.0 mL, 2 mmol) was stirred at 95° C. for 18 h. The resulting solution was cooled to room temperature and poured into a solution of ethyl acetate and water (1:1, 50 mL). The layers were separated. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica using ethyl acetate/hexanes 3:7 as eluent to yield 2-[2-(4,4-difluoro-cyclohexyl)-vinyl]-5-(2-fluoro-6-trifluoromethyl-phenyl)-1H-benzimidazole.

후처리

  1. customThe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica

출처 및 근거

ORD 기록
ord-c23cb18f734d479bb366fb41ea118daa
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08217060B2

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