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

HRID 892213ノート

反応式

HRID 892213 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-34de95c285ca4640bd6a7858a7e76018
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

反応ノート

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