HCID 9967388, compound → 1-Benzyl-3-(5-hydroxymethylfur-2-yl)indazole

HRID 1743354Notes

Reaction equation

HRID 1743354 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](OC)=[O:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[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]([CH2:22][OH: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 1

HCID 9967388HCID 9967388, compound

Product 1

HCID 57121-Benzyl-3-(5-hydroxymethylfur-2-yl)indazoleYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-3-(5-methoxycarbonyl-2-furyl)-1H-indazole in THF (150 mL) was added dropwise to a suspension of CaBH4.2THF (3.9 g, 18.23 mmol) in THF (150 mL) at room temperature. The resultant mixture was heated to reflux for 15 h. The reaction mixture was allowed to cool, then poured slowly onto brine. The layers were separated and the aqueous layer was extracted three times with ether. The combined organic material was dried (MgSO4) and concentrated under reduced pressure. The crude product was chromatographed on silica (30–40% EtOAc/cyclohexane) and then recrystallised (ethanol/H2O) to give the product as fine cream needles (1.56 g, 86%): mp 112–112.5° C. (lit. mp 108–109° C.); MS (EI) M+ 304; 1H-NMR (CDCl3) 4.76 (s, 2H), 5.68 (s, 2H), 6.50 (d, 1H, J=3.3 Hz), 6.90 (d, 1H, J=3.3 Hz), 7.21–7.40 (m, 8H), 8.08 (d, 1H, J=8.5 Hz); 13C-NMR (CDCl3) 54.12, 58.53, 108.87, 110.57, 110.59, 122.25, 122.38,122.50, 127.83, 128.00(2C), 128.72, 129.68(2C), 137.14, 137.53, 141.45, 149.52, 154.88; Anal. (C19H16N2O2) C, calcd 74.98; found 74.80, H, calcd 5.30; found 5.28, N, calcd 9.20; found 9.15.

Workup

  1. customat room temperature
  2. temperatureto reflux for 15 h
  3. temperatureto cool
  4. additionpoured slowly onto brine
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted three times with ether
  7. dry with materialThe combined organic material was dried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was chromatographed on silica (30–40% EtOAc/cyclohexane)
  10. customrecrystallised (ethanol/H2O)

Sources & evidence

ORD record
ord-ab81dcb47f4f44bd920ef90a943a28bb
Source dataset
uspto-grants-2006_03
Patent number
US07009056B2

Reaction notes

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