Sodium hydride → 3-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-hexanoic acid ethyl ester

HRID 24044

반응식

HRID 24044 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[N:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:25]([O:27][C:28](=[O:35])[CH2:29][CH:30](Br)[CH2:31][CH2:32][CH3:33])[CH3:26]>CN(C=O)C>[CH2:25]([O:27][C:28](=[O:35])[CH2:29][CH:30]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[N:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH2:31][CH2:32][CH3:33])[CH3:26]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 225702772-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridineHCID 22570372Ethyl-beta-bromocaproate

생성물 1

HCID 668213643-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-hexanoic acid ethyl ester수율 17%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridine (0.18 g, 0.62 mmol) in DMF (2 mL) was added sodium hydride (30.0 mg, 1.24 mmol) at room temperature. After stirring for 15 minutes, 3-bromo-hexanoic acid ethyl ester (276 mg, 1.24 mmol) was added. The reaction mixture was stirred overnight and quenched with water. The crude product was extracted with methylene chloride, washed with brine, and purified via column chromatography with silica gel (ethyl acetate/hexane:1:1), to give the title product (17% yield). 1H NMR (CDCl3) δ 9.08 (dd, J=1.7, 4.0 Hz, 1H), 8.14 (m, 1H), 8.06 (m, 1H), 7.32-7.44 (m, 4H), 7.05-7.12 (m, 2H), 6.45 (d, J=3.2 Hz, 1H), 4.81 (m, 1H), 3.99 (m, 2H), 3.08 (m, 2H), 2.83 (m, 4H), 2.22 (m, 2H), 1.90 (m, 2H), 1.20 (m, 2H), 1.07 (m, 3H), 0.87 (m, 3H). Mass Spectrum (LCMS, ESI) calculated for C27H32N3O2 430.3 (M+H); found 430.3.

후처리

  1. stirringThe reaction mixture was stirred overnight
  2. customquenched with water
  3. extractionThe crude product was extracted with methylene chloride
  4. washwashed with brine
  5. custompurified via column chromatography with silica gel (ethyl acetate/hexane:1:1)

출처 및 근거

ORD 기록
ord-301af04e9db84a50b66dc225119971a0
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855722B2

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