5-Bromo-2-nitropyridine → tert-butyl (3S)-3-methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

HRID 1022267Notes

Reaction equation

HRID 1022267 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.Br[C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[N:20][CH:21]=1>>[CH3:1][C@@H:2]1[N:7]([C:16]2[CH:21]=[N:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3]1

Participants

3

Reactant 2

HCID 8176205-Bromo-2-nitropyridineHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 86683728tert-butyl (3S)-3-methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylateYield 50%

Procedure

Following the procedure of Example 323a, and starting with (3S)-tert-butyl 3-methylpiperazine-1-carboxylate (10.0 g, 50 mmol) and 5-bromo-2-nitropyridine (10.5 g, 50 mmol) afforded 340a as a yellow solid (8.05 g, 50%). MS-ESI: [M+H]+ 323

Sources & evidence

ORD record
ord-ea93e6ea1c8e403fb60668114460a20a
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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