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

HRID 1159777ノート

反応式

HRID 1159777 の反応式
[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

参加物

4

反応物 2

HCID 27631784-Bromo-1H-indole-3-carbaldehyde2 回HCID 21226445Aluminium lithium hydride

生成物 1

HCID 529877044-Bromo-3-methyl-1H-indole収率 92.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-93ec121d0840423bbab25d5c676b2366
出典データセット
uspto-grants-2010_10
特許番号
US07812017B2

反応ノート

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