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

HRID 36896노트

반응식

HRID 36896 반응식
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

참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 19936624HCID 19936624, 화합물HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-1f17195807d04142a0764a98cbb30cf2
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418242

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