Methanol → Methyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate

HRID 1913942노트

반응식

HRID 1913942 반응식
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([O:21][CH2:22]C2C=CC=CC=2)=[O:20])[CH:3]=1.CO.C[O-].[Na+]>O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[CH:3]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 70495788Benzyl 4-amino-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate

생성물 1

HCID 70495727Methyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Benzyl 4-amino-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate (3.00 g, 7.41 mmol) was added to CH3OH (35 mL). Sodium methoxide (25 wt % in CH3OH; 2.0 mL, 8.9 mmol) was added to the reaction mixture and allowed to stir for 24 h. Water (50 mL) was added to the reaction mixture and the mixture was concentrated under reduced pressure to remove most of the CH3OH. The mixture was extracted with EtOAc (2×40 mL), and the combined organic layers were washed with water (40 mL) and satd sodium chloride (40 mL) and concentrated under reduced pressure to provide methyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate as a pale yellow solid (1.86 g; 67% purity by LC area).

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto remove most of the CH3OH
  3. extractionThe mixture was extracted with EtOAc (2×40 mL)
  4. washthe combined organic layers were washed with water (40 mL) and satd sodium chloride (40 mL)
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c31acb30b611444f8f59674691b7a836
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609855B2

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