Pyrrolidine → 1H-Indole,5-[2-(phenylmethoxy)ethoxy]-

HRID 23992ノート

反応式

HRID 23992 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([N+]([O-])=O)=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:22]1CCC[CH2:23]1>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:16][CH:17]=1)[NH:22][CH:23]=[CH:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 31268PyrrolidineHCID 69734823HCID 69734823、化合物

生成物 1

HCID 167382491H-Indole,5-[2-(phenylmethoxy)ethoxy]-収率 22%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21584119Ethylacetate methanol溶媒

反応条件

温度
120 °C

実験手順

5 (2-Benzyloxy-ethoxy)-2-nitro-toluene (12.4 g, 43.0 mmol), N-N-dimethylformamide dimethyl acetal (6.55 g, 51.6 mmol) and pyrrolidine (3.68 g, 51.6 mmol) were dissolved in N-N-dimethylformamide (25 mL). The mixture was heated to 120° C. for 16 h. The solvent was evaporated under vacuum and the crude reaction was dissolved in 70% ethyl acetate/methanol (250 mL). The reaction was placed in a Parr Hydrogenator under a hydrogen atmosphere for 16 h with 10% palladium on carbon [10% w/w] (3.00 g) at 50 psi. The reaction was filtrated over celite and the crude mixture was purified via column chromatography with silica gel eluting with hexane/ethyl acetate to give the title compound (22% yield). 1H NMR (CDCl3) δ 7.27-7.41 (m, 6H), 7.19 (t, 1H, J=2.5 Hz), 7.13 (d, 1H, J=2.3 Hz), 6.91 (dd, 1H, J=2.5, 8.8 Hz), 6.48 (m, 1H), 4.67 (s, 2H), 4.21 (m, 2H), 3.87 (m, 2H).

後処理

  1. customThe solvent was evaporated under vacuum
  2. customthe crude reaction
  3. filtrationThe reaction was filtrated over celite
  4. customthe crude mixture was purified via column chromatography with silica gel eluting with hexane/ethyl acetate

出典と根拠

ORDレコード
ord-a0537e5de5884f2bb8522ffa3b0f0c7a
出典データセット
uspto-grants-2005_02
特許番号
US06855722B2

反応ノート

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