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

HRID 913962노트

반응식

HRID 913962 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb0d8e20971a4927ac5db3fc09e2e391
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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