Ethylene Glycol → HCID 22480359, compound

HRID 1594251Notes

Reaction equation

HRID 1594251 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C[OH:29]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]([O:24][CH2:25][CH2:26][OH:29])=[O:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 174Ethylene GlycolHCID 15408136HCID 15408136, compound

Product 1

HCID 22480359HCID 22480359, compound

Procedure

200 mg (0.6 mmol) of 1-benzyl-3-(5-ethoxycarbonyl-2-furyl)indazole were dissolved in ethylene glycol and heated under reflux for 1.5 h. For work-up, the mixture was concentrated using a rotary evaporator and the crude product was chromatographed over silica gel using hexane/ethyl acetate (1:1). This gave 68 mg (31%) of the title compound. 1H-NMR (D6-DMSO): δ=3.72 (q, 2H, CH2—OH), 4.31 (t, 2H, CH2—C —OH), 4.93 (t, 1H, OH), 6.78 (s, 2H, CH2-phenyl), 7.23 (d, 1H, H-3′), 7.23-7.40 (m, 6H, phenyl-H, H-5), 7.50 (d, 1H, H-4′), 7.50 (t, 1H, H-6), 7.83 (d, 1H, H-7), 8.16 (d, 1H, H-4).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 h
  3. concentrationFor work-up, the mixture was concentrated
  4. customa rotary evaporator
  5. customthe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-a2ff9cae7af349358ceb13477efd74b7
Source dataset
uspto-grants-2007_11
Patent number
US07300950B2

Reaction notes

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