Ethyl Acetate → ethyl 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutanoate

HRID 1847586ノート

反応式

HRID 1847586 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[C:12]#[C:13][C:14]([CH3:22])([CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(OCC)(=O)C>CC#N.Cl[Pd]Cl>[F:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:12]=[C:13]([C:14]([CH3:21])([CH3:22])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:1]2)=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

参加物

5

反応物 2

HCID 8857Ethyl AcetateHCID 59129516Ethyl 5-(2-amino-4-fluoro-5-nitrophenyl)-3,3-dimethylpent-4-ynoate

生成物 1

HCID 59129505ethyl 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutanoate収率 100.3%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 6342Acetonitrile溶媒

実験手順

To a mixture of ethyl 5-(2-amino-4-fluoro-5-nitrophenyl)-3,3-dimethylpent-4-ynoate (34.5 g, 0.11 mol) and PdCl2 (10.4 g, 58.6 nmol) in CH3CN (350 mL) was heated to reflux for 1.5 hours. The reaction mixture was cooled down to room temperature. Ethyl acetate (300 mL) was added, the precipitate was filtered off and washed with methanol. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 40:1) to give ethyl 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutanoate (34.0 g, 98%) as a deep yellow solid. 1H NMR (300 MHz, CDCl3) δ 10.11 (brs, 1H), 8.30 (d, J=7.2 Hz, 1H), 7.14 (d, J=11.7 Hz, 1H), 6.35 (d, J=1.5 Hz, 1H), 4.17 (q, J=7.2 Hz, 2H), 2.69 (s, 2H), 1.51 (s, 6H), 1.25 (t, J=7.2 Hz, 3H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. filtrationthe precipitate was filtered off
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 40:1)

出典と根拠

ORDレコード
ord-8ff05056e4be4a24b8fd0dd583aa8348
出典データセット
uspto-grants-2015_02
特許番号
US08952050B2

反応ノート

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