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Water → methyl 5-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate

HRID 709808
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HRID 709808 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:19]([OH:20])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1.Br[CH2:22][CH:23]1[CH2:28][CH2:27][O:26][C:25]([CH3:30])([CH3:29])[CH2:24]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:29][C:25]1([CH3:30])[CH2:24][CH:23]([CH2:22][O:20][C:19]2[C:10]([C:3]3[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=3[F:1])=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])[CH2:28][CH2:27][O:26]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 576996994-(Bromomethyl)-2,2-dimethyloxaneHCID 117759971Methyl 6-(2-fluoro-5-methoxyphenyl)-5-hydroxynicotinate

생성물 1

HCID 117760026methyl 5-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate수율 88.3%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of methyl 6-(2-fluoro-5-methoxyphenyl)-5-hydroxynicotinate (739 mg) and 4-(bromomethyl)-2,2-dimethyltetrahydro-2H-pyran (828 mg) in DMF (20 mL) was added potassium carbonate (736 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water (100 mL), and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (950 mg) as a colorless oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-24407a1bb0b84aafae52efeb242714df
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181186B2

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