Hydrochloric Acid → 2-(6-bromo-1H-indol-3-yl)acetonitrile

HRID 2215747노트

반응식

HRID 2215747 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11]N(C)C)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C-]#N.[Na+].[CH3:18][N:19](C=O)C.Cl>O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][C:18]#[N:19])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 133840941-(6-Bromo-1H-indol-3-yl)-N,N-dimethylmethanamine

생성물 1

HCID 158193282-(6-bromo-1H-indol-3-yl)acetonitrile수율 79%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

6-Bromo-N,N-dimethyl-1H-indole-3-methanamine (7.76 g, 30.6 mmol) and NaCN (1.95 g, 39.8 mmol, 1.30 eq.) were combined with DMF (40 mL) and water (40 mL). The mixture was heated to reflux for 6 hours, then cooled to rt. Aqueous 1N HCl (40 mL) was added, and the product was extracted with EtOAc. The organic layer was washed with water and dried (MgSO4). The solvent was removed in vacuo to give 5.70 g (79%) of the title compound, that was 79% pure by HPLC area, containing 14% 6-bromoindole. The material was used without purification in the subsequent step.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. extractionthe product was extracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-cc8d90fcc6be4ac29a20aa06ca04345e
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109229B2

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