Triphenylphosphine → 1-(3-Furylmethyl)-3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113769Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11](=[O:22])[NH:12][C:13](=[O:21])[C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[O:23]1[CH:27]=[CH:26][C:25]([CH2:28]O)=[CH:24]1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:23]1[CH:27]=[CH:26][C:25]([CH2:28][N:12]2[C:13](=[O:21])[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:11]2=[O:22])=[CH:24]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione (0.17 mmol, 50 mg), 3-furanmethanol (0.19 mmol, 18 mg), diethyl azodicarboxylate (0.19 mmol, 33 mg) in dry THF (1 mL) was added triphenylphosphine (0.19 mmol, 49 mg) in dry THF (1 mL). The mixture was heated in a microwave reactor at 130° C. for six min. After cooling, the reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN) to give 17 mg (27%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.61 (bs, 1H), 7.35 (bs, 1H), 7.16 (bs, 1H), 7.15-7.05 (m, 3H), 7.00-6.95 (m, 2H), 6.62-6.51 (m, 4H), 6.48 (bs, 1H), 4.63 (s, 2H), 3.69 (s, 3H).

Workup

temperatureAfter cooling
customthe reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

Sources & evidence

ORD record: ord-a702ada79ff14f188e0a02e6b708093c
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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