Dimethylformamide → Methyl N-methylindole-6-carboxylate

HRID 252832ノート

反応式

HRID 252832 の反応式
N1C2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=C1.[H-].[Na+].[CH3:15]I.[CH3:17][N:18]([CH3:21])[CH:19]=O>>[CH3:17][N:18]1[C:21]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:15])=[O:11])[CH:8]=2)[CH:3]=[CH:19]1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5952301H-indole-6-carboxylic acid

生成物 1

HCID 639843Methyl N-methylindole-6-carboxylate

実験手順

1H-Indole-6-carboxylic acid 37 (0.20 g, 1.24 mmol) was dissolved in dimethylformamide (10 mL) and cooled to 0° C. for the portion-wise addition of sodium hydride (0.20 g, 4.96 mmol). After complete addition, the reaction mixture was allowed to warm to rt and stirred for 1 hr then methyl iodide (0.15 mL, 2.48 mmol) was added to the reaction mixture. Quenching with water followed by rotary evaporation led to the crude residue, which was taken up with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and evaporated to provide crude 166 (it was used crude in the next step). MS: 189.08 (calc), 190.1 (obs).

後処理

  1. additionAfter complete addition
  2. customQuenching with water
  3. customfollowed by rotary evaporation
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto provide crude 166 (it

出典と根拠

ORDレコード
ord-92d41947951d4d30afe6093e0cee5ace
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

反応ノート

読み込み中…