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Ethyl Acetate → 2-Fluoro-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine

HRID 410240
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HRID 410240 반응식
FC(F)(F)S(O[C:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH:8]=1)(=O)=O.[F:19][C:20]1[C:25](B(O)O)=[CH:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:19][C:20]1[C:25]([C:7]2[CH2:16][CH2:15][C:10]3([O:11][CH2:12][CH2:13][O:14]3)[CH2:9][CH:8]=2)=[CH:24][CH:23]=[CH:22][N:21]=1
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참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 114830861,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate

생성물 1

HCID 576066882-Fluoro-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine

시약·촉매·용매 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

To a mixture of 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (10.2 g, 35.4 mmol) and 2-fluoropyridin-3-ylboronic acid (5.00 g, 35.5 mmol) in 1,2-dimethoxyethane (200 mL) and aqueous sodium carbonate (53.2 mL, 106 mmol, 2N) under argon atmosphere was added palladium tetrakis(triphenylphosphine) (1.23 g, 1.06 mmol). The mixture was heated and stirred at 85° C. for 1 h., then cooled to room temperature. Ethyl acetate was added and the mixture was washed with water, saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give 2-fluoro-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine. MS (ESI, pos. ion) m/z: 236.1 (M+1).

후처리

  1. temperatureThe mixture was heated
  2. temperaturecooled to room temperature
  3. washthe mixture was washed with water, saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting oil was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-adce9c92893c4828a2710cc2c257a06a
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08759532B2

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