5-Bromo-2-nitropyridine → HCID 67355586, compound

HRID 627417Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:19][CH2:18][CH2:17][C:11]2([O:15][C:14](=[O:16])[NH:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:21]1[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[N:25][CH:26]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:19][CH2:18][CH2:17][C:11]2([O:15][C:14](=[O:16])[N:13]([C:21]3[CH:26]=[N:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)[CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 8176205-Bromo-2-nitropyridine

HCID 67354794HCID 67354794, compound

Product 1

HCID 67355586HCID 67355586, compoundYield 92.4%

Procedure

Following general N—C coupling procedure 1, 2-oxo-1-oxa-3,8-diaza-spiro[4.6]undecane-8-carboxylic acid tert-butyl ester (0.510 g, 1.887 mmol) (Reference: German Patent DE10 2005 030051A1 (28 Dec. 2006)) was combined with 5-bromo-2-nitropyridine (0.400 g, 1.971 mmol, 1.05 eq) which gave 3-(6-Nitro-pyridin-3-yl)-2-oxo-1-oxa-3,8-diaza-spiro[4.6]undecane-8-carboxylic acid tert-butyl ester as a brown solid (0.684 g, 1.743 mmol) in 92% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.45 (br. s., 9H) 1.54-1.72 (m, 1H) 1.86-2.16 (m, 3H) 3.30 (d, J=8.03 Hz, 1H) 3.66 (br. s., 2H) 3.81 (d, J=9.03 Hz, 1H) 3.94 (d, J=7.53 Hz, 1H) 8.33 (d, J=9.03 Hz, 1H) 8.52 (br. s., 1H) 8.60 (dd, J=9.03, 3.01 Hz, 1H). MS m/z 337.1 (M+H)+

Sources & evidence

ORD record: ord-64777773fc4e491f84e6ee77b7588837
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309252B2

Reaction notes

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