Sodium Carbonate → 4-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine

HRID 1842517노트

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HRID 1842517 반응식
C(=O)([O-])[O-].[Na+].[Na+].[O:7]1[CH2:12][CH:11]=[C:10](B2OC(C)(C)C(C)(C)O2)[CH2:9][CH2:8]1.Br[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([F:29])[CH:24]=1.[Cl-].[NH4+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[O:7]1[CH2:12][CH:11]=[C:10]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([F:29])[CH:24]=2)[CH2:9][CH2:8]1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 27628514-Bromo-2-fluoropyridineHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

생성물 1

HCID 585484534-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine수율 89%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A mixture of tetrakis(triphenylphosphine)palladium(0) (0.20 g, 0.17 mmol), aqueous sodium carbonate (2N aqueous, 8.52 mL, 17.05 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.43 g, 6.82 mmol), and 4-bromo-2-fluoropyridine (1.0 g, 5.68 mmol) in 1,2-dimethoxyethane (25 mL) was placed under argon atmosphere using 3 evacuation/backfill cycles. The mixture was then heated to 80° C. for 16 h then cooled to RT. Ethyl acetate and saturated aqueous ammonium chloride were added and the layers of the resulting biphasic mixture were separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil that was purified by silica gel chromatography to give 4-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine (0.90 g, 5.0 mmol, 89% yield) as a light yellow solid.

후처리

  1. temperaturethen cooled to RT
  2. customthe layers of the resulting biphasic mixture were separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil that
  7. customwas purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-790dc212df1144088b1cb610fa84feae
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946230B2

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