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2,6-Lutidine → Methyl 2-(1,3-benzodioxol-5-yl)-2-[6-(hydroxymethyl)1-methyl-1H-3-indolyl]acetate

HRID 1934612
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HRID 1934612 반응식
CC1C=CC=C(C)N=1.[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH:18](Br)[C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:12]=2[O:11][CH2:10]1.[OH:24][CH2:25][C:26]1[CH:34]=[C:33]2[C:29]([CH:30]=[CH:31][N:32]2[CH3:35])=[CH:28][CH:27]=1>CN(C)C=O>[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH:18]([C:30]3[C:29]4[C:33](=[CH:34][C:26]([CH2:25][OH:24])=[CH:27][CH:28]=4)[N:32]([CH3:35])[CH:31]=3)[C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:12]=2[O:11][CH2:10]1
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참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetateHCID 18673032(1-Methyl-1H-indol-6-yl)methanol

생성물 1

HCID 22467201Methyl 2-(1,3-benzodioxol-5-yl)-2-[6-(hydroxymethyl)1-methyl-1H-3-indolyl]acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

2,6-Dimethylpyridine (0.12 ml) was added to a stirred solution of methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate (from step (c), 273 mg, 1 mmol) and 6-(hydroxymethyl)-1-methylindole (from step (a), 161 mg, 1 mmol) in anhydrous dimethylformamide (2 ml) at ambient temperature, under a nitrogen atmosphere. The solution was heated to 80° C. for 3 hours. The reaction mixture was cooled, and partitioned between diethylether and water, separated and the organic layer dried (magnesium sulphate) and evaporated in vacuo. The residue was flash chromatographed (using diethyl ether as eluant) to live the subtitle compound as a colourless foam (273 mg).

후처리

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between diethylether and water
  3. customseparated
  4. dry with materialthe organic layer dried (magnesium sulphate)
  5. customevaporated in vacuo
  6. customchromatographed (using diethyl ether as eluant)

출처 및 근거

ORD 기록
ord-3ff28bc8397e4b5ca800d5644a567452
출처 데이터셋
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06384070B2

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