Trimethylaluminum → 6-Bromo-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline

HRID 1693074ノート

反応式

HRID 1693074 の反応式
CS(O[C:6]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Br:22])[CH:18]=2)[N:13]=1)([CH3:11])[C:7]([F:10])([F:9])[F:8])(=O)=O.[CH3:23][Al](C)C>C1CCCCC1>[Br:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:6]([CH3:23])([CH3:11])[C:7]([F:10])([F:9])[F:8])[CH:21]=[CH:20]2

参加物

4

反応物 2

HCID 16682925TrimethylaluminumHCID 574581676-Bromoquinolin-2-yl-2,2,2-trifluoro-1-methylethyl methanesulfonate

生成物 1

HCID 574581686-Bromo-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline収率 85%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

実験手順

To a suspension of 1-(6-bromoquinolin-2-yl)-2,2,2-trifluoro-1-methylethyl methanesulfonate (1.40 g, 3.52 mmol) in cyclohexane (14 ml) was added trimethylaluminum (14 ml, 14 mmol, 1.03M in hexane solution) at room temperature, and the mixture was stirred at room temperature for 16 hours. The reaction was carefully quenched with saturated sodium bicarbonate aqueous solution (10 ml), brine (10 ml) and diluted with ethyl acetate (100 ml). After the mixture was stirred for 30 minutes, formed precipitate was removed by celite and washed with ethyl acetate. The filtrate was concentrated and purified through silica gel column chromatography, eluting with hexane only, to furnish the title compound (951 mg, 85% yield) as colorless oil. 1H NMR (300 MHz, CDCl3) δ 1.72 (6H, s), 7.66 (1H, d, J=8.8 Hz), 7.75-7.80 (1H, m), 7.96-8.00 (2H, m), 8.06 (1H, d, J=8.8 Hz). MS (ESI): m/z 318, 320 (M+H)+.

後処理

  1. customThe reaction was carefully quenched with saturated sodium bicarbonate aqueous solution (10 ml), brine (10 ml)
  2. additiondiluted with ethyl acetate (100 ml)
  3. stirringAfter the mixture was stirred for 30 minutes
  4. customformed precipitate
  5. customwas removed by celite
  6. washwashed with ethyl acetate
  7. concentrationThe filtrate was concentrated
  8. custompurified through silica gel column chromatography
  9. washeluting with hexane only

出典と根拠

ORDレコード
ord-9476238cf1374cd2a1091aaee93deee7
出典データセット
uspto-grants-2012_04
特許番号
US08158650B2

反応ノート

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