Acetic Acid → HCID 86703280, compound

HRID 2409959Notes

Reaction equation

HRID 2409959 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[NH:7][C:8]3[C:13]([C:14]=2[CH:15](O)[C:16]2[N:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=[C:10]([O:27][CH3:28])[CH:9]=3)=[CH:2]1.C(O)(=O)C>CO.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[NH:7][C:8]3[C:13]([C:14]=2[CH2:15][C:16]2[N:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=[C:10]([O:27][CH3:28])[CH:9]=3)=[CH:2]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86703281HCID 86703281, compound

Product 1

HCID 86703280HCID 86703280, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 6-[(2-furan-3-yl-6-methoxy-1H-indol-3-yl)hydroxymethyl]pyridine-2-carboxylate (590 mg) and a boran-2-picoline complex (175 mg) in methanol (3 mL) was added acetic acid (3 mL), and this mixture was stirred at room temperature for 8 hours. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (386 mg). 1H-NMR (CDCl3) δ ppm: 3.85 (3H, s), 4.05 (3H, s), 4.48 (2H, s), 6.62-6.67 (1H, m), 6.76 (1H, dd, J=2.3, 8.5 Hz), 6.87-6.91 (1H, m), 7.17-7.23 (1H, m), 7.34 (1H, d, J=8.5 Hz), 7.47-7.52 (1H, m), 7.62 (1H, t, J=7.8 Hz), 7.78-7.84 (1H, m), 7.90-8.06 (2H, m).

Workup

  1. washwashed with 5% aqueous sodium hydrogen carbonate solution and saturated brine successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-fc992c822a9f4fb791ce5dfabae65d27
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

Loading…