tert-Butyl 1H-pyrrolo(3,2-c)pyridine-1-carboxylate → 1-tert-butoxycarbonyl-5-[1-(2-chlorophenyl)-6-methylheptyl]-1H-pyrrolo[3,2-c]pyridin-5-ium bromide

HRID 1801547Notes

Reaction equation

[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.C(O[C:20](=O)[C:21](C)([CH3:36])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([Br:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34])C)C>C(#N)C>[Br-:35].[C:13]([O:12][C:10]([N:1]1[C:9]2[CH:8]=[CH:7][N+:6]([CH:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]([CH3:36])[CH3:20])=[CH:5][C:4]=2[CH:3]=[CH:2]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (0.81 g, 3.73 mmol), 7-bromo-7-(2-chlorophenyl)-2,2-dimethyloctanoic acid ethyl ester (1.40 g, 3.73 mmol) in acetonitrile (25 mL) was stirred and warmed to 45° C. After 52 hours, the reaction was completed. The solvent was evaporated under reduced pressure, the residue was washed with diethyl ether (3×20 mL) to afford 1-tert-butoxycarbonyl-5-[1-(2-chlorophenyl)-6-methylheptyl]-1H-pyrrolo[3,2-c]pyridin-5-ium bromide (1.47 g, 66.5% yield) as a yellow oil. 1H NMR (Field: 300 MHz, Solvent: CD3OD/TMS) δ (ppm): 10.54 (s, 1H), 8.84 (d, 1H, J=6.9 Hz), 8.23 (d, 1H, J=7.8 Hz), 7.72 (s, 1H), 7.53 (t, 1H, J=4.2 Hz), 7.45 (t, 1H, J=7.2 Hz), 7.39 (d, 1H, J=3.6 Hz), 7.31 (s, 1H), 6.96 (s, 1H), 6.47 (t, 1H, J=7.2 Hz), 4.10 (q, 2H, J=5.7 Hz), 2.72 (d, 2H, J=6.6 Hz), 2.40 (m, 1H), 1.69 (s, 9H), 1.50-1.32 (m, 4H), 1.21 (t, 3H, J=3.3 Hz), 1.12 (s, 6H). (crude mixture. HRMS (DIP-CI): failed, decomposed on analysis.

Workup

customThe solvent was evaporated under reduced pressure
washthe residue was washed with diethyl ether (3×20 mL)

Sources & evidence

ORD record: ord-c027ea390ee04c17aef2922b0814aac3
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349833B2

Reaction notes

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