Methanol → 6-Chloro-N-[(3-Fluorophenyl)-methyl]-2-methoxy-4-methyl-pyridine-3-carboxylic acid amide

HRID 1753869노트

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HRID 1753869 반응식
[H-].[Na+].Cl[C:4]1[C:9]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[O:11])=[C:8]([CH3:21])[CH:7]=[C:6]([Cl:22])[N:5]=1.[OH2:23].[CH3:24]O>>[Cl:22][C:6]1[N:5]=[C:4]([O:23][CH3:24])[C:9]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[O:11])=[C:8]([CH3:21])[CH:7]=1

참가 물질

5

반응물 4

HCID 887Methanol2회HCID 962WaterHCID 24758Sodium hydrideHCID 866643132,6-dichloro-N-(3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide

생성물 1

HCID 866643196-Chloro-N-[(3-Fluorophenyl)-methyl]-2-methoxy-4-methyl-pyridine-3-carboxylic acid amide수율 54%

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온도
70 °C

실험 절차

330 mg (8.3 mmol, 60% w/w in mineral oil) NaH were slowly added to Methanol (30 ml) at RT and stirring was continued at RT for 45 min. Then 2.35 g (7.5 mmol) 2,6-dichloro-N-(3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide (synthesis is described in section a) of example 2) were added and the RM was heated to 70° C. for 24 h. After cooling to RT water (10 ml) was added and most of the MeOH was removed in vacuo. The mixture was then extracted with EtOAc and the organic layer was washed twice with brine, dried over MgSO4 and concentrated in vacuo. Crystallisation (hexane/EtOAc 3:1) of the residue yielded 1.24 g (0.4 mmol, 54%) 6-Chloro-N-[(3-Fluorophenyl)-methyl]-2-methoxy-4-methyl-pyridine-3-carboxylic acid amide.

후처리

  1. additionwere added
  2. customwas removed in vacuo
  3. extractionThe mixture was then extracted with EtOAc
  4. washthe organic layer was washed twice with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customCrystallisation (hexane/EtOAc 3:1) of the residue

출처 및 근거

ORD 기록
ord-0f4fdb93759a4b178fae655765b3d25f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09168259B2

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