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

HRID 12614노트

반응식

HRID 12614 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b898882e96cb45c1803327a8130cdd74
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728023B2

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