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

HRID 1964465노트

반응식

HRID 1964465 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 6342Acetonitrile용매

실험 절차

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, 1 H), 8.30 (d, J=7.2 Hz, 1 H), 7.14 (d, J=11.7 Hz, 1 H), 6.35 (d, J=1.5 Hz, 1 H), 4.17 (q, J=7.2 Hz, 2 H), 2.69 (s, 2 H), 1.51 (s, 6 H), 1.25 (t, J=7.2 Hz, 3 H).

후처리

  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)

출처 및 근거

ORD 기록
ord-d62dc80428934a40af7eadecc2e21ce7
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415387B2

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