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 931391Notes

Reaction equation

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

Participants

Conditions

Temperature: 23 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-e493929efb204bef8e856d43851c845a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296750B2

Reaction notes

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