4-(Difluoromethoxy)aniline → 3-{[4-(Difluoromethoxy)phenyl]amino}-4-phenyl-1-(pyridin-3-ylmethyl)-1H-pyrrole-2,5-dione

HRID 2113761Notes

Reaction equation

[F:1][CH:2]([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.Cl[C:13]1[C:14](=[O:32])[N:15]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[C:16](=[O:24])[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:13]2[C:14](=[O:32])[N:15]([CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[C:16](=[O:24])[C:17]=2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 140 °C

Procedure

4-(Difluoromethoxy)aniline (0.94 mmol, 149 mg) dissolved in dry CH3CN (2.3 mL) was added to crude 3-chloro-4-phenyl-1-(pyridin-3-ylmethyl)-1H-pyrrole-2,5-dione (0.39 mmol, 115 mg) and the reaction mixture was subjected to microwave heating single node 140° C., one h. The reaction mixture was purified using HPLC (57% 0.1M ammonium acetate buffer: 43% CH3CN→100% CH3CN, 20 mL/min) to give 122 mg (75%) of the title compound. 1H NMR (400 MHz, CD3CN) δ 8.63 (d, 1H), 8.51 (dd,1H), 7.92 (bs, 1H), 7.79-7.74 (m, 1H), 7.34 (dd, 1H), 7.20-7.07 (m, 3H), 7.00-6.94 (m, 2H), 6.78 (s, 4H), 6.59 (t, J=74.1 Hz, 1H), 4.76 (s, 2H).

Workup

customThe reaction mixture was purified

Sources & evidence

ORD record: ord-e2918eee13bf4608a3bee6ac2cd0797b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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