Water → 4-Iodo-2-methoxypyridine-3-carboxylic acid

HRID 1034934

반응식

HRID 1034934 반응식
[I:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([O:10][CH3:11])[N:5]=[CH:4][CH:3]=1.CC(=CC)C.O.Cl([O-])=[O:19].[Na+]>CC(O)(C)C>[I:1][C:2]1[C:7]([C:8]([OH:19])=[O:9])=[C:6]([O:10][CH3:11])[N:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 105532-Methyl-2-buteneHCID 100383814-Iodo-2-methoxynicotinaldehydeHCID 23668197Sodium Chlorite

생성물 1

HCID 184399404-Iodo-2-methoxypyridine-3-carboxylic acid

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

To a solution of 4-iodo-2-methoxynicotinaldehyde (1 g, 3.58 mmol) in t-BuOH (6 mL), cooled at 25° C., is added 2-methyl-2-butene (6 mL, 2 M solution), Na2HPO4 (1.2 g) and water (3 mL). The reaction mixture is stirred for 5 minutes and sodium chlorite (800 mg, 8.9 mmol) is added slowly. Stirring of the mixture is continued until the aldehyde is completely consumed (3 hours, monitored by LCMS). The reaction is quenched with aq. formic acid. The mixture is partitioned between ethyl acetate (100 mL) and the organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The white powder was used for the next reaction without any further purification. 1H NMR 400 MHz (DMSO-d6) δ 10.06 (s, 1H), 7.89 (d, 1H, J=5.6 Hz), 7.48 (d, 1H, J=5.6 Hz), 3.87 (s, 1H); MS m/z 294.1 (M+1). MS m/z 280.01 (M+1).

후처리

  1. stirringStirring of the mixture
  2. customis completely consumed (3 hours, monitored by LCMS)
  3. customThe reaction is quenched with aq. formic acid
  4. customThe mixture is partitioned between ethyl acetate (100 mL)
  5. washthe organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe white powder was used for the next reaction without any further purification

출처 및 근거

ORD 기록
ord-9a313dd65a38467894278503abdde5f1
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546370B2

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