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

HRID 1897585노트

반응식

HRID 1897585 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-e094975e23ec4295983ec8e9febc6db8
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519134B2

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