2-Bromo-6-hydrazinopyridine → tert-Butyl 3-(2-(6-bromopyridin-2-yl)hydrazono)-9-azabicyclo[3.3.1]nonane-9-carboxylate

HRID 469692Notes

Reaction equation

HRID 469692 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[N:3]=1.O=[C:11]1[CH2:18][CH:17]2[N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:13]([CH2:14][CH2:15][CH2:16]2)[CH2:12]1>CCO>[Br:1][C:2]1[N:3]=[C:4]([NH:8][N:9]=[C:11]2[CH2:18][CH:17]3[N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:13]([CH2:14][CH2:15][CH2:16]3)[CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 193925882-Bromo-6-hydrazinopyridineHCID 45790088N-Boc-9-azabicyclo[3.3.1]nonan-3-one

Product 1

HCID 58092251tert-Butyl 3-(2-(6-bromopyridin-2-yl)hydrazono)-9-azabicyclo[3.3.1]nonane-9-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-6-hydrazinylpyridine (393 mg, 2.09 mmol) and tert-butyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate (500 mg, 2.09 mmol) were heated at reflux in EtOH (5 mL) for 16 h and the mixture concentrated to provide the title compound (855 mg, 100%) as a yellow solid: ESI MS m/z 409 [M+H]+.

Workup

  1. concentrationthe mixture concentrated

Sources & evidence

ORD record
ord-829ac8bf9f6f458888ad37ef8b3fbbbd
Source dataset
uspto-grants-2014_01
Patent number
US08629158B2

Reaction notes

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