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Dimethyl Sulfoxide → Methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate

HRID 1481705
ノート
印刷プレビュー

反応式

HRID 1481705 の反応式
N1C=CC=CC=1.CS(C)=O.[CH2:11]([C:13]1[C:14]([C:25]2[CH:26]=[CH:27][C:28]3[N:29]([CH:31]=[C:32]([CH2:34][OH:35])[N:33]=3)[CH:30]=2)=[N:15][C:16]([O:23][CH3:24])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])[CH3:12].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:11]([C:13]1[C:14]([C:25]2[CH:26]=[CH:27][C:28]3[N:29]([CH:31]=[C:32]([CH:34]=[O:35])[N:33]=3)[CH:30]=2)=[N:15][C:16]([O:23][CH3:24])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])[CH3:12]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl Sulfoxide2 回HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 71284396Methyl 5-ethyl-6-(2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate

生成物 1

HCID 89423055Methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate収率 79%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

反応条件

温度
0 °C

実験手順

To SO3-pyr complex (0.320 g, 2.01 mmol) was added pyridine (0.16 mL, 2.02 mmol) and DMSO (0.36 mL, 5.07 mmol). Slurry was stirred at room temperature 10 min before DCM (2.0 mL) was added and mixture was cooled to 0° C. Then solution of methyl 5-ethyl-6-(2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate (0.346 g, 1.01 mmol), Hunig's base (0.60 mL, 3.44 mmol) and DMSO (0.36 mL, 5.07 mmol) in DCM (4.0 mL) was added dropwise. Reaction mixture was stirred at 0° C. 30 min and LC/MS showed complete consumption of starting material. DCM was removed under reduced pressure and residue was treated with H2O (10 mL). Solid which was formed was collected by filtration affording methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate (0.270 g) in 79% yield.

後処理

  1. additionwas added
  2. customReaction mixture
  3. custom30 min and LC/MS
  4. customconsumption of starting material
  5. customDCM was removed under reduced pressure and residue
  6. additionwas treated with H2O (10 mL)
  7. customSolid which was formed
  8. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-02bf8e1feada4ce0a4c7224adea59084
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409905B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート