Acetic Acid → HCID 69096878, compound

HRID 2409957Notes

Reaction equation

HRID 2409957 reaction equation
O[CH:2]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[NH:15][C:14]=1[C:24]1[CH:28]=[C:27]([CH3:29])[S:26][CH:25]=1)[C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1.C(O)(=O)C>CO.C(OCC)(=O)C>[CH3:23][O:22][C:18]1[CH:17]=[C:16]2[C:21]([C:13]([CH2:2][C:3]3[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=3)=[C:14]([C:24]3[CH:28]=[C:27]([CH3:29])[S:26][CH:25]=3)[NH:15]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86703278HCID 86703278, compound

Product 1

HCID 69096878HCID 69096878, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 6-{hydroxy-[6-methoxy-2-(5-methylthiophen-3-yl)-1H-indol-3-yl]methyl}pyridine-2-carboxylate (335 mg) and a boran-2-picoline complex (92.1 mg) in methanol (1.7 mL) was added acetic acid (1.7 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 (255 mg). 1H-NMR (CDCl3) δ ppm: 2.48-2.53 (3H, m), 3.85 (3H, s), 4.05 (3H, s), 4.54 (2H, s), 6.74 (1H, dd, J=2.2, 8.6 Hz), 6.88 (1H, d, J=2.2 Hz), 6.96-7.01 (1H, m), 7.17-7.22 (2H, m), 7.29 (1H, d, J=8.6 Hz), 7.62 (1H, t, J=7.8 Hz), 7.93-7.98 (1H, m), 8.01 (1H, br s).

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-7718587d922042fea9b85bfcee442b3e
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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