2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-(Hydroxymethyl)-1'-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 931391노트

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HRID 931391 반응식
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.COC1C=CC(C[O:22][CH2:23][C:24]2[CH:25]=[C:26]3[CH2:49][C:31]4([C:39]5[C:34](=[N:35][CH:36]=[CH:37][CH:38]=5)[N:33]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:32]4=[O:48])[O:30][C:27]3=[N:28][CH:29]=2)=CC=1>ClCCl.O>[OH:22][CH2:23][C:24]1[CH:25]=[C:26]2[CH2:49][C:31]3([C:39]4[C:34](=[N:35][CH:36]=[CH:37][CH:38]=4)[N:33]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:45])([CH3:46])[CH3:47])[C:32]3=[O:48])[O:30][C:27]2=[N:28][CH:29]=1

참가 물질

5

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 900505505-(((4-Methoxybenzyl)oxy)methyl)-1'-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

생성물 1

HCID 1317351675-(Hydroxymethyl)-1'-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
23 °C

실험 절차

DDQ (0.533 g, 2.35 mmol) was added to a solution of 5-(((4-methoxybenzyl)oxy)methyl)-1′-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (0.61 g, 1.2 mmol) in dichloromethane (16 mL) and water (4 mL) at 0° C. The resulting mixture was gradually warmed to 23° C. and stirred for 1 h, then partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 50% ethyl acetate in petroleum ether to give the title compound as a racemic mixture. MS: m/z=400.2 (M+1).

후처리

  1. custompartitioned between saturated aqueous sodium bicarbonate solution and dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel eluting with 50% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-e493929efb204bef8e856d43851c845a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296750B2

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