Hydrochloric Acid → 5-Formyl-1H-indole-3-carbonitrile

HRID 2355949노트

반응식

HRID 2355949 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]#[N:12].[H-].[Na+].C([Li])(CC)C.C1CCCCC1.Cl.[C:27](=O)(O)[O-:28].[Na+]>CN(C)C=O.O1CCCC1>[CH:27]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]#[N:12])=[O:28]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 8078CyclohexaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 36233545-Bromo-3-cyanoindoleHCID 178418400CID 53628100

생성물 1

HCID 211022025-Formyl-1H-indole-3-carbonitrile수율 72%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

5-Bromo-1H-indole-3-carbonitrile (4.25 g, 19.23 mmol) and sodium hydride (0.51 g, 21.2 mmol) were weighed into a flame-dried round-bottom flask containing a magnetic stir bar. Under a nitrogen atmosphere at room temperature, dry tetrahydrofuran (24 mL) was added. The mixture was stirred at room temperature for 15 min, during which time it became homogeneous. The stirred mixture was cooled to −78° C. and a solution of sec-butyllithium in cyclohexane (1.4M, 30.2 mL, 2.2 equiv) was added over several minutes. After 1 h at −78° C., dimethylformamide (6.0 mL) was slowly added and the mixture allowed to warm to room temperature overnight. The solution was cooled to 0° C. and carefully treated with 1 N hydrochloric acid (45 mL). After a few minutes, solid sodium bicarbonate was added until a pH of 9-10 was attained. The two layers were separated and the aqueous phase washed twice with ethyl acetate. The combined organic layers were washed with water (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography gave 2.4 g (72%) of pure material. LC/MS: tR=0.99 min, 171.07 (MH)+.

후처리

  1. additioncontaining a magnetic stir bar
  2. temperatureThe stirred mixture was cooled to −78° C.
  3. waitAfter 1 h at −78° C.
  4. temperatureto warm to room temperature overnight
  5. temperatureThe solution was cooled to 0° C.
  6. waitAfter a few minutes
  7. customThe two layers were separated
  8. washthe aqueous phase washed twice with ethyl acetate
  9. washThe combined organic layers were washed with water (2×), brine (2×)
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3de9f2a07e4f4ad681363e0f148a6987
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754732B2

반응 노트

불러오는 중…