Water → HCID 68452677, compound

HRID 2356184Notes

Reaction equation

[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=[O:18])[CH3:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=1)[CH:8]=2)[CH3:2].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.O.[O-]S([O-])(=O)=O.[Mg+2]>CN(C)C(=O)C.C(Cl)Cl.C(OC(=O)C)C.CCCCCC>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=[O:18])[CH3:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:22][CH:21]=1)[CH:8]=2)[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

To 1-[9-Ethyl-6-(4-fluoro-benzoyl)-9H-carbazol-3-yl]-ethanone (1.30 g; 25.6 mmol) in N,N-Dimethylacetamide (DMA) (10 ml) is added morpholine (1.07 g; 12.3 mmol) at 100° C. This reaction mixture is stirred at 140° C. for 15 h. After the reaction is completed, the reaction mixture is poured into H2O, then, a beige solid was obtained by filtration. The solid is dissolved in CH2Cl2, followed by dying over anhydrous MgSO4. Condensation under reduced pressure affords a beige solid as crude product. (1.13 g) The pure product was obtained by silica gel column chromatography with ethylacetate/hexane (1/3-1/1) as eluent. (1.03 g, 67%). The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ[ppm]: 1.50 (t, 3H), 2.72 (s, 3H), 3.36 (t, 4H), 3.89 (t, 4H), 4.44 (q, 2H), 6.96 (d, 2H), 7.48 (dd, 2H), 7.86 (dd, 2H), 8.05 (dd, 1H), 8.16 (dd, 1H), 8.58 (d, 1H), 8.73 (d, 1H).

Workup

customa beige solid was obtained by filtration
customCondensation under reduced pressure
customaffords a beige solid as crude product

Sources & evidence

ORD record: ord-7aac4d0fe5194b139eec3763e762d29e
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759043B2

Reaction notes

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