5-Bromo-2-nitropyridine → HCID 89614521, compound

HRID 1850616Notes

Reaction equation

HRID 1850616 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[NH:17][CH2:16][C@@H:15]2[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][C@@H:14]2[CH2:13]1>>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:17]2[C:12](=[O:11])[CH2:13][C@H:14]3[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][C@H:15]3[CH2:16]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 8176205-Bromo-2-nitropyridineHCID 89614646HCID 89614646, compound

Product 1

HCID 89614521HCID 89614521, compoundYield 85%

Procedure

Following general N—C coupling procedure 1, 5-bromo-2-nitropyridine and cis-tert-butyl 6-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate were combined and gave after purification cis-tert-butyl 5-(6-nitropyridin-3-yl)-6-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (1.0 g) in 85% yield. 1H NMR (400 MHz, CDCl3) δ ppm 8.58 (d, J=2.53 Hz, 1H), 8.28 (d, J=8.59 Hz, 1H), 8.07 (dd, J1=8.84, J2=2.27 Hz, 1H), 4.18-3.61 (m, 4H), 3.29 (m, 2H), 2.85 (m, 3H), 2.55 (m, 1H), 1.47 (s, 9H)

Workup

  1. customgave
  2. customafter purification cis-tert-butyl 5-(6-nitropyridin-3-yl)-6-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (1.0 g) in 85% yield

Sources & evidence

ORD record
ord-f84edeb643a94c3a9723e89d9b5e46b1
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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