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

HRID 1842517ノート

反応式

HRID 1842517 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-790dc212df1144088b1cb610fa84feae
出典データセット
uspto-grants-2015_02
特許番号
US08946230B2

反応ノート

読み込み中…