5-Bromo-2-nitropyridine → HCID 67356011, compound

HRID 1850625Notes

Reaction equation

HRID 1850625 reaction equation
[C:1]1(=[O:11])[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][CH2:8][CH2:9][CH:10]=[C:2]12.Br[C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[N:17][CH:18]=1>>[N+:19]([C:16]1[N:17]=[CH:18][C:13]([N:6]2[CH2:5][CH2:4][N:3]3[CH2:7][CH2:8][CH2:9][CH2:10][CH:2]3[C:1]2=[O:11])=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

3

Reactant 2

HCID 8176205-Bromo-2-nitropyridineHCID 13049391HCID 13049391, compound

Product 1

HCID 67356011HCID 67356011, compoundYield 81%

Procedure

Following general N—C coupling procedure 1, hexahydro-pyrido[1,2-a]pyrazin-1-one (0.300 g, 1.945 mmol), was combined with 5-bromo-2-nitropyridine (0.395 g, 1.945 mmol, 1.0 eq), and gave 2-(6-Nitro-pyridin-3-yl)-hexahydro-pyrido[1,2-a]pyrazin-1-one (0.481 g, 1.567 mmol) in 81% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.27-1.53 (m, 2H) 1.54-1.61 (m, 4H) 1.66-1.81 (m, 1H) 1.94 (d, J=12.55 Hz, 1H) 2.22 (td, J=11.80, 3.01 Hz, 1H) 2.39 (d, J=12.55 Hz, 1H) 2.68-2.83 (m, 2H) 2.96-3.12 (m, 2H) 3.49 (d, J=3.51 Hz, 1H) 3.56 (dd, J=10.79, 2.26 Hz, 1H) 4.16 (td, J=11.29, 4.52 Hz, 1H) 8.13 (dd, J=8.53, 2.51 Hz, 1H) 8.29 (d, J=8.53 Hz, 1H) 8.68 (d, J=2.51 Hz, 1H); MS m/z 277.2 (M+H)+.

Sources & evidence

ORD record
ord-74e57f1712a7443ebcbb7d11a6188e10
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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