N-Methyl-N-(pyridine-2-yl)formamide → 5-(Benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde

HRID 625969ノート

反応式

HRID 625969 の反応式
[CH2:1]([O:8][C:9]1[C:10](=[O:18])[N:11]([CH3:17])[C:12](Br)=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.CN(C1C=CC=CN=1)[CH:26]=[O:27]>C1COCC1>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[N:11]([CH3:17])[C:12]([CH:26]=[O:27])=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 572611N-Methyl-N-(pyridine-2-yl)formamideHCID 67418185HCID 67418185、化合物HCID 178418918HCID 178418918、化合物

生成物 1

HCID 866754905-(Benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde収率 84.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a −78° C. solution of 3-(benzyloxy)-5,6-dibromo-1-methylpyridin-2(1H)-one (1.5 g, 4.02 mmol) in THF (20 mL) was added 2 M isopropylmagnesium chloride in THF (4.02 mL, 8.04 mmol) dropwise. This mixture was stirred at −78° C. for 15 minutes under nitrogen, and N-methyl-N-pyridin-2-ylformamide (1.4 mL, 12.06 mmol) was added. The mixture was allowed to slowly warm to room temperature overnight. Volatiles were removed under reduced pressure, and the resulting residue was partitioned between dilute aqueous hydrochloric acid and ethyl acetate. The aqueous layer was removed and discarded. The organic layer was collected, dried over anhydrous magnesium sulfate, and purified by silica gel chromatography to afford 5-(benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde (1.09 g, 3.38 mmol, 84% yield). ES-MS (M+H)+=323.

後処理

  1. temperatureto slowly warm to room temperature overnight
  2. customVolatiles were removed under reduced pressure
  3. customthe resulting residue was partitioned between dilute aqueous hydrochloric acid and ethyl acetate
  4. customThe aqueous layer was removed
  5. customThe organic layer was collected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-975b92a1dad04d289fe25a2fe9fad3de
出典データセット
uspto-grants-2016_04
特許番号
US09309199B2

反応ノート

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