Potassium Carbonate → HCID 85865444, compound

HRID 494745Notes

Reaction equation

Br[C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[N:12]1([CH2:17][CH2:18][CH2:19][NH2:20])[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCO.[Pd]>[N:12]1([CH2:17][CH2:18][CH2:19][NH:20][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[NH2:8])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 90 °C

Procedure

1.300 g (5.940 mmol) 3-bromo-4-nitro-pyridine-1-oxide and 0.980 g (7.430 mmol) 3-pyrrolidin-1-yl-propylamine was added to a suspension of 0.820 g (5.940 mmol) potassium carbonate in 20 mL DMF and the mixture was stirred for 3 hours at 90° C. The solvent was evaporated i. vac. and the residue purified by column chromatography (Alox (neutral, activity II-III), gradient dichloromethane/MeOH 100:0→95:5 v/v) (0.950 g, 60% of theory). 0.900 g (3.380 mmol) of the intermediate product was added to a suspension of 300 mg Pd/C in 10 mL EtOH and the mixture was hydrogenated for 4.5 hours at RT and 50 psi H2-pressure. The catalyst was removed by filtration and the filtrate evaporated i. vac. The product is present in admixture with the corresponding pyridine-N-oxide and was used in the next reaction step without any further purification.

Workup

customThe solvent was evaporated i
customand the residue purified by column chromatography (Alox (neutral, activity II-III), gradient dichloromethane/MeOH 100:0→95:5 v/v) (0.950 g, 60% of theory)
waitthe mixture was hydrogenated for 4.5 hours at RT
customThe catalyst was removed by filtration
customthe filtrate evaporated i
customwas used in the next reaction step without any further purification

Sources & evidence

ORD record: ord-d46c52631fc44624b590825efb5a55d7
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538115B2

Reaction notes

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