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

HRID 23992노트

반응식

HRID 23992 반응식
[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

참가 물질

5

반응물 2

HCID 31268PyrrolidineHCID 69734823HCID 69734823, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21584119Ethylacetate methanol용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a0537e5de5884f2bb8522ffa3b0f0c7a
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855722B2

반응 노트

불러오는 중…