1,2-Dichloroethane → HCID 86663042, compound

HRID 2410789Notes

Reaction equation

ClCCCl.[N:5]([C:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[N:16][C:15]([Br:25])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[N+]=[N-]>C1COCC1.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh]>[Br:25][C:15]1[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]2[NH:5][C:19]3[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=3[C:17]=2[N:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.2-Dichloroethane (4.4 mL) was added to a mixture of methyl 3-azido-6-bromo-2-(4-chlorophenyl)isonicotinate (2.42 g, 6.58 mmol), rhodium octanoate dimer (0.41 g, 0.53 mmol) and crushed 4A° molecular sieves (2.5 gm) and heated at 80° C. for 24 hr. The reaction was diluted with THF and filtered. The collected solid was washed with multiple portions of hot THF to extract remaining product. The solvent was removed from the combined filtrates and the residue was suspended in MeOH and the product was collected by filtration to leave methyl 2-bromo-7-chloro-5H-pyrido[3,2-b]indole-4-carboxylate (1.92 g, 5.65 mmol, 86% yield) as a gray solid. MS (ESI) m/z 340.99 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.89 (1H, s), 8.19 (1H, d, J=8.24 Hz), 7.92 (1H, s), 7.76 (1H, d, J=1.53 Hz), 7.35 (1H, dd, J=8.55, 1.83 Hz), 4.04 (3H, s).

Workup

customcrushed 4A° molecular sieves (2.5 gm)
filtrationfiltered
washThe collected solid was washed with multiple portions of hot THF
extractionto extract
customThe solvent was removed from the combined filtrates
filtrationthe product was collected by filtration

Sources & evidence

ORD record: ord-fd085c3114644b7ab964f53dc302cf4d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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