5-Bromo-2-nitropyridine → HCID 67377326, compound

HRID 627433Notes

Reaction equation

HRID 627433 reaction equation
C([O:5][C:6]([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][NH:11][C:12](=[O:17])[CH2:13]2)=[O:7])(C)(C)C.Br[C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[N:23][CH:24]=1>>[N+:25]([C:22]1[N:23]=[CH:24][C:19]([N:11]2[C:12](=[O:17])[CH2:13][CH:14]3[N:8]([C:6]([OH:5])=[O:7])[CH:9]([CH2:16][CH2:15]3)[CH2:10]2)=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

3

Reactant 2

HCID 8176205-Bromo-2-nitropyridineHCID 585748429-Boc-4-oxo-3,9-diaza-bicyclo[4.2.1]nonane

Product 1

HCID 67377326HCID 67377326, compoundYield 58%

Procedure

Following general N—C coupling procedure 1, 4-Oxo-3,9-diaza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester, 1.86 g (7.72 mmoles) was combined with 5-Bromo-2-nitro-pyridine, 1.51 g (7.42 mmoles), which after recrystallized from CH2Cl2-Heptanes gave 3-(6-Nitro-pyridin-3-yl)-4-oxo-3,9-diaza bicyclo[4.2.1]nonane-9-carboxylic acid tea-butyl ester, (1.59 g) in 58% yield. TLC Rf ˜0.45 (75% Ethyl acetate-Heptane)

Workup

  1. customafter recrystallized from CH2Cl2-Heptanes

Sources & evidence

ORD record
ord-2987c6acd24d471c9d00aa40b8dad4df
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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