Ethyl bromoacetate → {3-[3-(Quinolin-2-ylmethoxy)-benzyl]-indol-1-yl}-acetic acid

HRID 892213노트

반응식

HRID 892213 반응식
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:14]=[C:15]([CH:28]=[CH:29][CH:30]=2)[O:16][CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:4]1.Br[CH2:32][C:33]([O:35]CC)=[O:34]>CN(C=O)C>[N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[CH2:17][O:16][C:15]1[CH:14]=[C:13]([CH:30]=[CH:29][CH:28]=1)[CH2:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:3]([CH2:32][C:33]([OH:35])=[O:34])[CH:4]=1

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 222415112-[3-(1H-Indol-3-ylmethyl)-phenoxymethyl]-quinoline

생성물 1

HCID 22241553{3-[3-(Quinolin-2-ylmethoxy)-benzyl]-indol-1-yl}-acetic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (60%, 22 mg, 0.55 mmol) is added to a solution of 2-[3-(1H-indol-3-ylmethyl)-phenoxymethyl]-quinoline (90 mg, 0.25 mmol, example 90) in DMF (2.5 mL). After stirring 5 minutes ethyl bromoacetate (0.1 mL, 0.9 mmol) is added and the reaction is allowed to stir 2 h. The reaction is partitioned between ethyl acetate and ammonium chloride and the organic phase is washed with water. The organic phase is dried over magnesium sulfate, concentrated and then the solid is titurated with ethyl ether and ethyl acetate to provide the title compound as a solid. m.p. 151–159° C.; 1H NMR (300 MHz, CDCl3) δ 8.20 (t, 2H), 7.83–7.80 (m, 1H), 7.77–7.71 (m, 1H), 7.67 (d, 1H), 7.61–7.53 (m, 1H), 7.45–7.42 (m, 1H), 7.29–7.14 (m, 3H), 7.05–6.99 (m, 2H), 6.94 (s, 1H), 6.85 (m, 2H), 5.16 (s, 2H), 4.84(s, 2H), 4.11 (s, 2H); MS (ESI) 423 (M+H)+.

후처리

  1. additionis added
  2. customThe reaction is partitioned between ethyl acetate and ammonium chloride
  3. washthe organic phase is washed with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-34de95c285ca4640bd6a7858a7e76018
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

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