N-methyl-2-pyrrolidone → ethyl 5-cyano-6-methoxy-1H-indole-2-carboxylate

HRID 400730ノート

反応式

HRID 400730 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[NH:7][C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5]2.[CH3:18][N:19]1C(=O)CCC1>>[C:18]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[NH:7][C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5]2)#[N:19]

参加物

3

反応物 2

HCID 13387N-methyl-2-pyrrolidoneHCID 14916489ethyl 5-bromo-6-methoxy-1H-indole-2-carboxylate

生成物 1

HCID 67401331ethyl 5-cyano-6-methoxy-1H-indole-2-carboxylate

反応条件

温度
200 °C

実験手順

A mixture of ethyl 5-bromo-6-methoxy-1H-indole-2-carboxylate obtained in step 1 (300 mg; 1.01 mmol) and cuprous cyanide (108 mg; 1.21 mmol) in NMP (10 mL) was heated under microwave irradiations at 200° C. for 30 minutes. The dark solution was filtered through a short pad of silica, which was washed with DCM. The obtained dark red solution was concentrated in vacuo and the oily residue was precipitated in water. The solid was collected by filtration, washed thoroughly with water and dried under high vacuum. Purification by silica column chromatography (DCM then DCM/MeOH, 99/1) gave the title compound as a slightly pink solid. HPLC (Method A), Rt 3.45 min (Purity: 97.4%). LC/MS (Method B): 243.2 (M+H)+.

後処理

  1. filtrationThe dark solution was filtered through a short pad of silica, which
  2. washwas washed with DCM
  3. concentrationThe obtained dark red solution was concentrated in vacuo
  4. customthe oily residue was precipitated in water
  5. filtrationThe solid was collected by filtration
  6. washwashed thoroughly with water
  7. customdried under high vacuum
  8. customPurification by silica column chromatography (DCM

出典と根拠

ORDレコード
ord-ff301c68923e4af2aa5f2f58aeb2400e
出典データセット
uspto-grants-2014_06
特許番号
US08741923B2

反応ノート

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