Methanol → Methyl 4-bromo-1H-indole-3-carboxylate

HRID 12614ノート

反応式

HRID 12614 の反応式
[CH3:1][OH:2].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH:13]=[O:14])=[CH:7][NH:8]2.[C-]#N.[Na+]>[O-2].[O-2].[Mn+4].C(OCC)(=O)C>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([C:13]([O:2][CH3:1])=[O:14])=[CH:7][NH:8]2

参加物

6

反応物 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 27631784-Bromo-1H-indole-3-carbaldehyde

生成物 1

HCID 13499091Methyl 4-bromo-1H-indole-3-carboxylate

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a methanol (40 mL) solution of 4-bromo-1H-indole-3-carboaldehyde [Chem. Pharm. Bull. 33,3696 (1985)] (395 mg), sodium cyanide (432 mg) and manganese dioxide (15.3 g) were sequentially added and the mixture was stirred overnight at room temperature. To the reaction mixture, ethyl acetate (50 mL) was added and insoluble matters were removed. The filtrate was concentrated and water was added to the residue, and then the solution was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried and then concentrated. The residue was washed with diisopropyl ether and n-hexane and then concentrated to obtain the titled compound having the following physical properties (375 mg).

後処理

  1. custominsoluble matters were removed
  2. concentrationThe filtrate was concentrated
  3. additionwater was added to the residue
  4. extractionthe solution was extracted with ethyl acetate
  5. washThe organic layer was washed in turn with water and saturated saline
  6. customdried
  7. concentrationconcentrated
  8. washThe residue was washed with diisopropyl ether and n-hexane
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-b898882e96cb45c1803327a8130cdd74
出典データセット
uspto-grants-2010_06
特許番号
US07728023B2

反応ノート

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