5-Bromo-2-nitropyridine → HCID 67354882, compound

HRID 1850648Notes

Reaction equation

HRID 1850648 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[O:11]=[C:12]1[CH2:19][CH:18]2[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:15]([CH2:16][CH2:17]2)[CH2:14][NH:13]1>>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:13]2[C:12](=[O:11])[CH2:19][CH:18]3[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:15]([CH2:16][CH2:17]3)[CH2:14]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

3

Reactant 2

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

Product 1

HCID 67354882HCID 67354882, compoundYield 78.4%

Procedure

Following general N—C coupling procedure 1, 5-Bromo-2-nitropyridine (1 gm, 4.93 mmol) was combined with tert-butyl 4-oxo-3,9-diazabicyclo[4.2.1]nonane-9-carboxylate (1.18 gm, 4.93 mmol) which gave tert-butyl 3-(6-nitropyridin-3-yl)-4-oxo-3,9-diazabicyclo[4.2.1]nonane-9-carboxylate (1.4 gm) in 78% yield.

Sources & evidence

ORD record
ord-947dba06b2524e85bc83e1805aa9d70d
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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