4-Fluorobenzoyl chloride → HCID 10406579, compound

HRID 1094618Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[C:18]2[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2].[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C.ClCCCl>[CH2:1]([O:3][C:4]([CH:6]1[C:18]2[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH2:9][CH2:8][N:7]1[C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([F:19])=[CH:21][CH:22]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

The title compound was prepared by the addition of 2,3,4,9-tetrahydro-1H-betacarboline-1-carboxylic acid ethyl ester (102 mg, 418 μmol), DCE (5 mL), 4-fluorobenzoyl chloride (60 μL, 477 μmol), diisopropyl ethylamine (167 μL, 954 μmol), DMAP (6 mg, 10 mol %) to a 25 mL flask. The solution was allowed to stir at 55° C. under N2 for 17 hours. The solution was concentrated under reduced pressure, and the crude material was chromatographed (SiO2, 100% hexane to 25% EtOAc) to provide 143 mg (63% yield) of title compound; 1H NMR (CDCl3) δ 8.40 (1H, br s), 7.53-7.57 (3H, m), 7.41 (1H, d), 7.10-7.23 (4H, m), 6.19 (1H, s), 4.31 (2H, m), 4.10 (1H, dd), 3.63 (1H, m), 2.87-2.96 (1H, m), 2.78 (1H, dd), 1.36 (3H, t); 13C NMR (CDCl3) 6171, 169, 138, 130, 129, 126, 126, 123, 120, 116, 116, 112, 110, 62, 53, 45, 22, 14; MS (ESI): 367 (MH+).

Workup

concentrationThe solution was concentrated under reduced pressure
customthe crude material was chromatographed (SiO2, 100% hexane to 25% EtOAc)

Sources & evidence

ORD record: ord-57e62c7a5ef240639bca8c087d669ff6
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133992B2

Reaction notes

Loading…