Cesium carbonate → 3-{[2-({3-Chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)phenyl]ethyl}-1-methylimidazolidine-2,4-dione

HRID 1797327Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[O:9])=[C:4]([Cl:17])[CH:3]=1.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][N:27]1[C:31](=[O:32])[CH2:30][N:29]([CH3:33])[C:28]1=[O:34].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:17][C:4]1[CH:3]=[C:2]([NH:1][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][CH2:26][N:27]2[C:31](=[O:32])[CH2:30][N:29]([CH3:33])[C:28]2=[O:34])[CH:7]=[CH:6][C:5]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:9]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (4-amino-2-chlorophenyl)(2-methylphenyl)methanone (61 mg. 0.25 mmol) (disclosed in WO 01/42189 A1), compound 436 (89 mg, 0.30 mmol), BINAP (5 mg), Pd2(dba)3 (5 mg) and Cs2CO3 (114 mg, 0.35 mmol) in 1,4-dioxane (5 ml) was heated to 120° C. under stirring for 3 days. The reaction mixture was filtered. The obtained solution was concentrated in vacuo. The residue was purified by chromatography (petroleum ether/ethyl acetate 1:1) to provide the desired product, which was not pure. The impure product was further purified by preparative TLC (petroleum ether/ethyl acetate 2:1) to give the pure title compound as brownish oil.

Workup

filtrationThe reaction mixture was filtered
concentrationThe obtained solution was concentrated in vacuo
customThe residue was purified by chromatography (petroleum ether/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-8c01a3d927a24472a597fc8e4b75397c
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034015B2

Reaction notes

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