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

HRID 1159777노트

반응식

HRID 1159777 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH:17]=O)=[CH:11][NH:12]2>C1COCC1>[Br:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH3:17])=[CH:11][NH:12]2

참가 물질

4

반응물 2

HCID 27631784-Bromo-1H-indole-3-carbaldehyde2회HCID 21226445Aluminium lithium hydride

생성물 1

HCID 529877044-Bromo-3-methyl-1H-indole수율 92.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

LAH (1.0M in THF, 5.75 mL, 5.75 mmol) was added dropwise to refluxing 4-bromo-1H-indole-3-carbaldehyde (644 mg, 2.87 mmol; Intermediate 27) in dry THF (20 mL). The mixture was refluxed 1 h, allowed to attain rt. and quenched with water (220 μL), W/w 15% aq. NaOH (220 μL) and water (650 μL). The resulting precipitation was filtered off, the filtrate concentrated and the residue was extracted with aq. NaOH (10 mL) and DCM (2×10 mL). The organic layers were combined with combined with an earlier batch of this intermediate (followed this experimental and starting from 4-bromo-1H-indole-3-carbaldehyde, 100 mg, 0.45 mmol; Intermediate 27), dried and concentrated to give the title compound (556 mg, 80%) as a light brown oil. MS (ESI+) for C9H8BrN m/z 210 (M+H)+.

후처리

  1. temperatureThe mixture was refluxed 1 h
  2. customto attain rt
  3. customand quenched with water (220 μL), W/w 15% aq. NaOH (220 μL) and water (650 μL)
  4. customThe resulting precipitation
  5. filtrationwas filtered off
  6. concentrationthe filtrate concentrated
  7. extractionthe residue was extracted with aq. NaOH (10 mL) and DCM (2×10 mL)
  8. dry with materialIntermediate 27), dried
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-93ec121d0840423bbab25d5c676b2366
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

반응 노트

불러오는 중…