Aluminium lithium hydride → 7-bromo-3-methyl-5-(trifluoromethyl)-1H-indole

HRID 913962ノート

反応式

HRID 913962 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]([C:19]([F:22])([F:21])[F:20])[CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH:17]=O>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([C:19]([F:22])([F:20])[F:21])[CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH3:17]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 575460277-bromo-5-(trifluoromethyl)-1H-indole-3-carbaldehyde

生成物 1

HCID 575461317-bromo-3-methyl-5-(trifluoromethyl)-1H-indole収率 57.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium aluminum hydride (16.98 ml, 16.98 mmol) was added to a −40° C. solution of 7-bromo-5-(trifluoromethyl)-1H-indole-3-carbaldehyde (1.24 g, 4.25 mmol) in THF (10 ml). The reaction was stirred between −30° C and −10° C. for 40 min and was quenched with saturated aqueous ammonium chloride (1 mL) and filtered through celite and washed with ethyl acetate (20 mL). The filtrate was evaporated and the residue was purified by chromatography on SiO2 with a gradient of 4% to 30% ethyl acetate/hexanes. The product 7-bromo-3-methyl-5-(trifluoromethyl)-1H-indole (677 mg, 2.435 mmol, 57.3% yield) was obtained as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 8.35 (s, 1H), 7.80(d, J=1.2 Hz, 1H), 7.57 (d, J=0.9 Hz, 1H), 7.12,(q, J=1.2 Hz, 1H), 2.33(d, J=1.2 Hz, 3H). LC (HPLC method 4): tR=3.45 min.

後処理

  1. customwas quenched with saturated aqueous ammonium chloride (1 mL)
  2. filtrationfiltered through celite
  3. washwashed with ethyl acetate (20 mL)
  4. customThe filtrate was evaporated
  5. customthe residue was purified by chromatography on SiO2 with a gradient of 4% to 30% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-fb0d8e20971a4927ac5db3fc09e2e391
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

反応ノート

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