Benzylamine → HCID 67286489, compound

HRID 218837Notes

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.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>N1C=CC=CC=1>[CH2:31]([NH:38][C:2]1[O:3][C:4]2[C:24]([OH:25])=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7]([C:8]1[CH:9]=[C:10]([O:18][CH3:19])[C:11]([O:16][CH3:17])=[C:12]([O:14][CH3:15])[CH:13]=1)=[O:20])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran (140 mg, 0.29 mmol) was dissolved in dry pyridine (2 mL) and benzylamine (500 μL, excess) was added to it and the reaction mixture was stirred at 80° C. for 1 hour. Solvent was distilled and the crude product was purified over silica gel column to afford the title compound as light yellow solid (112 mg, 83%); 1H NMR (300 MHz, CDCl3) δ: 9.27(b, 1H, NH), 7.39-7.32(m, 5Hs, Ar Hs), 6.96(s, 2H, benzoyl Hs), 6.61(d, 1H, J=8.47 Hz), 6.50(d, 1H, J=8.10 Hz), 4.83(d, 2H, J=4.95 Hz, Benzyl Hs), 3.91(s, 3H, OMe), 3.85(s, 3H, OMe), 3.84(s, 6H, 2×OMe).

Workup

distillationSolvent was distilled
customthe crude product was purified over silica gel column

Sources & evidence

ORD record: ord-47f3c563965d4ae7917d833119c96d00
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198466B2

Reaction notes

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