Boron tribromide → HCID 58102874, compound

HRID 384982Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12](=[O:28])[N:13]([CH:17]3[C:25]4[C:20](=[C:21]([O:26]C)[CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)[CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.B(Br)(Br)Br>C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12](=[O:28])[N:13]([CH:17]3[C:25]4[C:20](=[C:21]([OH:26])[CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)[CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-(4-bromophenyl)-1-(4-methoxy-2,3-dihydro-1H-inden-1-yl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.4 g, 0.91 mmol) in Ch2Cl2 (2 mL) at 0 C was added BBr3 (1M in CH2Cl2, 9 mL). The reaction was stirred at 0° C. for 1 hr. It was poured into sat. aqueous NaHCO3 (50 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organic layers were dried and concentrated to a solid. The solid was washed with MeOH and CH2Cl2 to afford a white solid. It was further purified by prep. HPLC to afford N-(4-bromophenyl)-1-(4-hydroxy-2,3-dihydro-1H-inden-1-yl)-2-oxo-1,2-dihydropyridine-3-carboxamide (120 mg, 31%). Retention time (min)=7.127, method [7], MS (ESI) 425.0 (M+H); 1H NMR (300 MHz, CDCl3) δ 12.19 (s, 1H), 8.61 (dd, J=2.1 Hz, 7.0 Hz, 1H), 7.68 (d, J=9.0 Hz, 2H), 7.47 (d, J=9.0 Hz, 2H), 7.15-7.30 (overlap with CDCl3, 2H), 6.81 (d, J=7.8 Hz, 1H), 6.72 (d, J=7.2 Hz, 1H), 6.60 (dd, J=5.4 Hz, 7.2 Hz, 1H), 6.41 (t, J=7.0 Hz, 1H), 5.0 (br, 1H), 2.80-3.10 (m, 3H), 1.98-2.15 (m, 1H).

Workup

extractionThe mixture was extracted with EtOAc (3×50 mL)
customThe combined organic layers were dried
concentrationconcentrated to a solid
washThe solid was washed with MeOH and CH2Cl2
customto afford a white solid
customIt was further purified by prep

Sources & evidence

ORD record: ord-d2e4e74ef45a468cb1131e1d29c5a958
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367836B2

Reaction notes

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