Carbon Dioxide → 1-methyl-3-[(1-methylpiperidin-4-yl)thio]-1H-indole-5-carboxylic acid

HRID 36896ノート

反応式

HRID 36896 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[S:12][CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.C([Li])CCC.[C:25](=[O:27])=[O:26]>C1COCC1>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:25]([OH:27])=[O:26])=[CH:10][CH:9]=2)[C:5]([S:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:6]1

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 19936624HCID 19936624、化合物HCID 178418339Butyllithium

生成物 1

HCID 199366641-methyl-3-[(1-methylpiperidin-4-yl)thio]-1H-indole-5-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-bromo-1-methyl-3-[(1-methylpiperidin-4-yl)thio]-1H-indole (19 g, prepared in Example 58) in THF (100 ml) is treated at -78° C. with a solution of butyllithium (31.5 ml, 2.5M in hexane). After 1 hour at this temperature, carbon dioxide is passed into the solution until it is saturated. After one hour, the reaction mixture is left to return to room temperature. The solvent is evaporated off and the residue is taken up with ether to give 1-methyl-3-[(1-methylpiperidin-4-yl)thio]-1H-indole-5-carboxylic acid (22.8 g) in the form of a yellow solid, which is used for the next step without purification.

後処理

  1. waitthe reaction mixture is left
  2. customto return to room temperature
  3. customThe solvent is evaporated off

出典と根拠

ORDレコード
ord-1f17195807d04142a0764a98cbb30cf2
出典データセット
uspto-grants-1995_05
特許番号
US05418242

反応ノート

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