3-Aminopyridine → HCID 24880182, compound

HRID 218840Notes

Reaction equation

HRID 218840 reaction equation
Br[C:2]1[O:3][C:4]2[C:24]([O:25]C(=O)C)=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1.[NH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1>C(#N)C.O>[OH:25][C:24]1[C:4]2[O:3][C:2]([NH:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[C:6]([C:7]([C:8]3[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=3)=[O:20])[C:5]=2[CH:21]=[CH:22][C:23]=1[O:29][CH3:30]

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Product 1

HCID 24880182HCID 24880182, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran (50 mg, 0.10 mmol) and 3-amino-pyridine (30 mg, 0.30 mmol) in a mixture of solvent acetonitrile:water (8:2, 5 mL) was refluxed with stirring for 6 hours. The solvent was distilled under vacuum and the residue was purified over silica gel column to afford the title compound as yellow solid (11 mg, 23%); 1H NMR (300 MHz, CDCl3) δ 11.22(s, 1H), 8.77(b, 1H), 8.42(b, 1H), 8.01(bd, 1H), 7.28(b, 1H), 7.03(s, 2H, benzoyl Hs), 6.71(d, 1H, J=8.82 Hz), 6.63(d, 1H, J=8.37 Hz), 3.94(s, 3H, OMe), 3.90(s, 3H, OMe), 3.86(s, 6H, 2×OMe).

Workup

  1. temperaturewas refluxed
  2. distillationThe solvent was distilled under vacuum
  3. customthe residue was purified over silica gel column

Sources & evidence

ORD record
ord-ebd512e356184587b1e32b98be89220c
Source dataset
uspto-grants-2012_06
Patent number
US08198466B2

Reaction notes

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