methyl E-4-[5-(3-carboxyprop-1-enyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate → HCID 14882687, 화합물

HRID 330208노트

반응식

HRID 330208 반응식
[C:1]([CH2:4]/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][CH2:17][CH3:18])[CH:11]=[C:10]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[O:30][CH3:31])([OH:3])=[O:2]>[Pd].C(OCC)(=O)C.O1CCCC1>[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][CH2:17][CH3:18])[CH:11]=[C:10]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[O:30][CH3:31])([OH:3])=[O:2]

참가 물질

5

반응물 1

HCID 67834906methyl E-4-[5-(3-carboxyprop-1-enyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

생성물 1

HCID 14882687HCID 14882687, 화합물수율 80.4%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Palladium on carbon (1.1 g, 10% w/w) was added to a solution of methyl E-4-[5-(3-carboxyprop-1-enyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (10.8 g) in ethyl acetate (300 ml) and tetrahydrofuran (100 ml), and the mixture hydrogenated at atmospheric pressure for 6 hr. The catalyst was removed by filtration through diatomaceous earth, the filter cake washed with ethyl acetate, and the combined filtrate evaporated. The residue was stirred in 1:4 ethyl acetate:hexane (150 ml) and the product isolated by filtration to give methyl 4-[5-(3-carboxypropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (8.72 g, 80%) as an off-white powder; mp 106°-109°; NMR (300 MHz, DMSO-d6): 0.81(t, 3H, CH3), 1.68-1.83(m, 4H), 2.20(t, 2H), 2.61(t, 2H), 3.83(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.02(m, 4H, NCH2, ArCH2Ar'), 6.92(d, 1H), 7.08(s, 1H), 7.23(m, 2H), 7.32(d, 1H), 7.44(m, 2H).

후처리

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washthe filter cake washed with ethyl acetate
  3. customthe combined filtrate evaporated
  4. customhexane (150 ml) and the product isolated by filtration

출처 및 근거

ORD 기록
ord-ea6f0aa570da4062979958ce1c67aa88
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894386

반응 노트

불러오는 중…