tert-Butyl 1H-pyrrolo(3,2-c)pyridine-1-carboxylate → 1-tert-butoxycarbonyl-5-[1-(2-chlorophenyl)-7-methyloctyl]-1H-pyrrolo[3,2-c]pyridin-5-ium bromide

HRID 1801534Notes

Reaction equation

HRID 1801534 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[C:20](=O)[C:21](C)([CH3:36])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([Br:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34])C>C(#N)C>[Br-:35].[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N+:13]([CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH:21]([CH3:20])[CH3:36])=[CH:12][C:11]=2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 20042876tert-Butyl 1H-pyrrolo(3,2-c)pyridine-1-carboxylateHCID 675129798-Bromo-8-(2-chlorophenyl)-2,2-dimethyloctanoic acid ethyl ester

Product 1

HCID 675180631-tert-butoxycarbonyl-5-[1-(2-chlorophenyl)-7-methyloctyl]-1H-pyrrolo[3,2-c]pyridin-5-ium bromideYield 68.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.81 g, 3.73 mmol), 8-bromo-8-(2-chlorophenyl)-2,2-dimethyloctanoic acid ethyl ester (1.44 g, 3.73 mmol), and acetonitrile (25 mL) were stirred at 45° C. for 52 hours. The solvent was evaporated under reduced pressure and residue was washed with diethyl ether (3×20 mL) to afford 1-tert-butoxycarbonyl-5-[1-(2-chlorophenyl)-7-methyloctyl]-1H-pyrrolo[3,2-c]pyridin-5-ium bromide (1.37 g, 60.6% yield) as a yellow oil. 1H NMR (Field: 300 MHz, Solvent: CD3OD/TMS) δ (ppm): 10.52 (s, 1H), 8.84 (d, 1H, J=7.2 Hz), 8.23 (d, 1H, J=7.8 Hz), 7.91 (t, 1H, J=3.6 Hz), 7.54-7.31 (m, 4H), 7.39 (s, 1H), 6.95 (s, 1H), 6.42 (t, 1H, J=7.2 Hz), 4.09 (q, 2H, J=7.2 Hz), 2.67 (m, 1H), 1.70 (s, 9H), 1.42-1.19 (m, 8H), 1.21 (t, 31-I, J=6.9 Hz), 1.10 (s, 6H). 13C NMR (Field: 75 MHz, Solvent: CDCl3/TMS) δ (ppm): 178.00, 147.44, 140.17, 136.60, 133.19, 131.97, 131.45, 130.42, 130.03, 128.64, 113.10, 108.61, 88.15, 71.55, 60.34, 42.23, 40.54, 34.54, 29.69, 28.13, 26.42, 25.28, 24.92, 14.46. HRMS (HR, DIP-CI): Calculated for C30H40ClN2O2 (M+H)+: not found (decomposed on analysis).

Workup

  1. customThe solvent was evaporated under reduced pressure and residue
  2. washwas washed with diethyl ether (3×20 mL)

Sources & evidence

ORD record
ord-3d547580fc5f4c5c947e4fa54b66c4f7
Source dataset
uspto-grants-2013_01
Patent number
US08349833B2

Reaction notes

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