Jones' reagent → 2'-Oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1',2'-dihydro-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxylic acid

HRID 931392Notes

Reaction equation

HRID 931392 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH2:15][C:16]1[CH:17]=[C:18]2[CH2:41][C:23]3([C:31]4[C:26](=[N:27][CH:28]=[CH:29][CH:30]=4)[N:25]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:24]3=[O:40])[O:22][C:19]2=[N:20][CH:21]=1>CC(C)=O>[O:40]=[C:24]1[N:25]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:37])([CH3:38])[CH3:39])[C:26]2=[N:27][CH:28]=[CH:29][CH:30]=[C:31]2[C:23]21[O:22][C:19]1=[N:20][CH:21]=[C:16]([C:15]([OH:3])=[O:14])[CH:17]=[C:18]1[CH2:41]2

Participants

4

Reactant 2

HCID 131709961Jones' reagentHCID 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

Product 1

HCID 900505402'-Oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1',2'-dihydro-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Freshly prepared Jones reagent was added drop wise to a solution of 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 (0.24 g, 0.60 mmol) in acetone (10 mL) at 0° C. until the starting material was completely consumed. The acidic mixture was neutralized carefully with saturated aqueous sodium bicarbonate solution and acidified with saturated aqueous citric acid solution to pH 5-6, then extracted with ethyl acetate (5×). The combined organic layers were dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 5% methanol in dichloromethane to give the title compound as a racemic mixture. MS: m/z=414.2 (M+1); 1H NMR (300 MHz, CD3OD): δ 8.70 (d, 1H, J=1.8 Hz), 8.34 (dd, 1H, J=1.5, 5.3 Hz), 8.29 (d, 1H, J=1.8 Hz), 7.89 (dd, 1H, J=1.5, 7.4 Hz), 7.19 (dd, 1H, J=5.3, 7.4 Hz), 5.26 (s, 2H), 3.78-3.65 (m, 4H), 0.95 (t, 2H, J=8 Hz), 0.005 (s, 9H).

Workup

  1. customwas completely consumed
  2. extractionextracted with ethyl acetate (5×)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-4758563854c1435ba7f785f96c2c97f4
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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