1-(5-Amino-1-benzofuran-2-yl)ethanone → 3-[(2-Acetyl-5-benzofuranyl)amino]-1-(2-methoxyethyl)-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113754Notes

Reaction equation

Cl[C:2]1[C:3](=[O:18])[N:4]([CH2:14][CH2:15][O:16][CH3:17])[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:19][C:20]1[CH:31]=[CH:30][C:23]2[O:24][C:25]([C:27](=[O:29])[CH3:28])=[CH:26][C:22]=2[CH:21]=1>CC#N>[C:27]([C:25]1[O:24][C:23]2[CH:30]=[CH:31][C:20]([NH:19][C:2]3[C:3](=[O:18])[N:4]([CH2:14][CH2:15][O:16][CH3:17])[C:5](=[O:13])[C:6]=3[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:21][C:22]=2[CH:26]=1)(=[O:29])[CH3:28]

Participants

Conditions

Temperature: 150 °C

Procedure

3-Chloro-1-(2-methoxyethyl)-4-phenyl-1H-pyrrole-2,5-dione (0.26 mmol, 70 mg) and 1-(5-aminobenzo[b]furan-2-yl)ethan-1-one (0.53 mmol, 92 mg) was dissolved in dry CH3CN (2 mL) and the reaction mixture was subjected to microwave heating single node 150° C. for 15 min and purified on SiO2 (EtOAc:heptane, 1:1) to give 18 mg (15%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.53 (bs, 1H), 7.40 (d, 1H), 7.24-7.09 (m, 5H), 7.06 (dd, 1H), 6.92 (d, 1H), 3.98 (t, J=5.6 Hz, 2H), 3.78 (t, J=5.6 Hz, 2H), 3.52 (s, 3H), 2.69 (s, 3H).

Workup

custompurified on SiO2 (EtOAc:heptane, 1:1)

Sources & evidence

ORD record: ord-4e638a193c954528920253ef6a4030d3
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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