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

HRID 922028ノート

反応式

HRID 922028 の反応式
[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

参加物

5

反応物 4

HCID 887Methanol2 回HCID 962WaterHCID 24758Sodium hydrideHCID 866643132,6-dichloro-N-(3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide

生成物 1

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

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ed584374279745f2aff0d5b7edff9062
出典データセット
uspto-grants-2016_03
特許番号
US09278103B2

反応ノート

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