Iodine → Methyl 5-hydroxy-6-iodopyridine-3-carboxylate

HRID 84584

반응식

HRID 84584 반응식
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[N:6][CH:5]=1.O1CCCC1.O.C(=O)([O-])[O-].[Na+].[Na+].[I:24]I>>[OH:10][C:8]1[C:7]([I:24])=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([O:2][CH3:1])=[O:11]

참가 물질

6

반응물 5

HCID 807IodineHCID 962WaterHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylate

생성물 1

HCID 57900098Methyl 5-hydroxy-6-iodopyridine-3-carboxylate수율 81.2%

실험 절차

To solution of 5-hydroxy-nicotinic acid methyl ester (2.50 g, 16.3 mmol) in tetrahydrofuran (50.0 mL, 616 mmol)/water (50.0 mL, 2780 mmol) was added sodium carbonate (5.19 g, 49.0 mmol) and iodine (10.4 g, 40.8 mmol). The reaction mixture was stirred at room temperature 4h. The aqueous layer containing product was separated and wash with hexane. The organic layer was neutralized to pH 7 with HCl, extracted EtOAc 4×. The combined organic layers was dried Na2SO4, concentrated. The crude product was purified by flash chromatography (EtOAc/DCM) (eluted at 40 EtOAc) to give methyl 5-hydroxy-6-iodonicotinate (81.2%) MS: (ESI+) 280.0

후처리

  1. additionThe aqueous layer containing product
  2. customwas separated
  3. washwash with hexane
  4. extractionextracted EtOAc 4×
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (EtOAc/DCM) (eluted at 40 EtOAc)

출처 및 근거

ORD 기록
ord-b7932e253f8748e3bb9398fb6e80e7a5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

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