4-Bromo-1H-indole-3-carbaldehyde → 4-Bromo-3-methyl-1H-indole

HRID 475266노트

반응식

HRID 475266 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:11]=O)=[CH:5][NH:6]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:11])=[CH:5][NH:6]2

참가 물질

4

반응물 2

HCID 27631784-Bromo-1H-indole-3-carbaldehydeHCID 21226445Aluminium lithium hydride

생성물 1

HCID 529877044-Bromo-3-methyl-1H-indole수율 75.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a refluxing solution of 4-bromo-1H-indole-3-carbaldehyde (644 mg, 2.87 mmol) in dry THF (20 mL) was added LiAlH4 (218 mg, 5.75 mmol) in several small portions. Heating at reflux was continued for 1 h, the reaction cooled to RT and quenched with water (220 μL), 15% aq. NaOH (w/w, 220 μL), and water (650 μL). The resulting precipitate was filtered and the filtrate was concentrated under reduced pressure to dryness. To the residue was added aq. NaOH (10 mL) and the solution twice extracted with DCM (2×10 mL). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford 454 mg (75%) of 4-bromo-3-methyl-1H-indole (230) as light brown oil: MS (ESI) m/z=210.1 [M+1]+

후처리

  1. temperatureHeating
  2. temperatureat reflux
  3. customquenched with water (220 μL), 15% aq. NaOH (w/w, 220 μL), and water (650 μL)
  4. filtrationThe resulting precipitate was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure to dryness
  6. additionTo the residue was added aq. NaOH (10 mL)
  7. extractionthe solution twice extracted with DCM (2×10 mL)
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-272d18d441bf4f5abccf56b9955905a0
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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