5-Bromo-2-nitropyridine → HCID 89614562, compound

HRID 1850614Notes

Reaction equation

HRID 1850614 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:16][CH2:15][C@H:14]2[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][C@@H:13]12>>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:16]2[C:12](=[O:11])[C@@H:13]3[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][C@@H:14]3[CH2:15]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 8176205-Bromo-2-nitropyridineHCID 67376140(3aR,6aR)-rel-Hexahydro-4-oxo-pyrrolo[3,4-c]pyrrole-2(1H)-carboxylic Acid 1,1-DiMethylethyl Ester

Product 1

HCID 89614562HCID 89614562, compoundYield 81.8%

Procedure

Following general N—C coupling procedure 1, 5-bromo-2-nitropyridine (4.71 g, 23.2 mmol, 1.05 eq) was combined with cis-tert-butyl 4-oxohexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (5 g, 22.1 mmol, 1.0 eq), which after silica gel purification gave cis-tert-butyl 5-(6-nitropyridin-3-yl)-4-oxohexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (6.3 g) in 81% yield. 1H NMR (400 MHz, CDCl3) δ ppm 8.75 (m, 2H), 8.34 (d, J=9.09 Hz, 1H), 4.20 (dd, J1=9.85 Hz, J2=6.82 Hz, 1H), 4.02-3.85 (m, 2H), 3.80 (d, J=10.11 Hz, 1H), 3.68 (m, 1H), 1.52-1.43 (m, 3H).

Workup

  1. customafter silica gel purification

Sources & evidence

ORD record
ord-0454a55a9d8f4161ad8861d1b13690b4
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

Loading…