Dimethylformamide → 3-Fluoro-5-(1-oxo-1,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde

HRID 1897585ノート

反応式

HRID 1897585 の反応式
[Li][CH2:2][CH2:3][CH2:4][CH3:5].C(N[CH:10]([CH3:12])[CH3:11])(C)C.Br[C:14]1[CH:15]=[N:16][CH:17]=[C:18]([F:20])[CH:19]=1.CN([CH:24]=[O:25])C.[C:26]([O-:29])(O)=[O:27].[Na+]>C1COCC1>[F:20][C:18]1[CH:17]=[N:16][CH:15]=[C:14]([C:5]2[CH:4]=[C:3]3[C:12](=[CH:10][CH:11]=2)[C:26](=[O:27])[O:29][CH2:2]3)[C:19]=1[CH:24]=[O:25]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 516892Sodium BicarbonateHCID 8202063-Bromo-5-fluoropyridineHCID 178418339Butyllithium

生成物 1

HCID 866748373-Fluoro-5-(1-oxo-1,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

n-BuLi (13.85 mL, 22.16 mmol) was added to a solution of diisopropylamine (3.16 mL, 22.16 mmol) in THF (50 mL) at −78° C. After 30 min, 3-bromo-5-fluoropyridine (3.0 g, 17.05 mmol) in THF (25 mL) was added dropwise. The mixture was stirred for 1 hr, and then DMF (3.96 mL, 51.1 mmol) was added dropwise. Saturated aqueous NaHCO3 was added and the cooling bath was removed. The mixture was shaken with ethyl acetate and the organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel flash chromatography employing dichloromethane-methanol, 9:1 to give 3-fluoro-5-(1-oxo-1,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.81 (d, J=1.4 Hz, 1H), 8.83 (s, 1H), 10.17 (s, 1H)

後処理

  1. customthe cooling bath was removed
  2. stirringThe mixture was shaken with ethyl acetate
  3. washthe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-e094975e23ec4295983ec8e9febc6db8
出典データセット
uspto-grants-2013_08
特許番号
US08519134B2

反応ノート

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