5-Bromo-2-nitropyridine → HCID 67356021, compound

HRID 1850632Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][CH2:16][C:10]2([O:14][C:13](=[O:15])[NH:12][CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[N:24][CH:25]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][CH2:16][C:10]2([O:14][C:13](=[O:15])[N:12]([C:20]3[CH:25]=[N:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)[CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 8176205-Bromo-2-nitropyridine

HCID 67357095HCID 67357095, compound

Product 1

HCID 67356021HCID 67356021, compoundYield 81.5%

Procedure

Following general N—C coupling procedure 1, 2-oxo-1-oxa-3,7-diaza-spiro[4.5]decane-7-carboxylic acid tert-butyl ester (0.546 g, 2.130 mmol) (Reference: German Patent DE10 2005 030051A1 (Dec. 28, 2006)), was combined with 5-bromo-2-nitropyridine (0.432 g, 2.130 mmol, 1.0 eq) which gave 3-(6-Nitro-pyridin-3-yl)-2-oxo-1-oxa-3,7-diaza-spiro[4.5]decane-7-carboxylic acid tert-butyl ester as a brown solid (0.709 g, 1.735 mmol) in 81% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.46 (br. s., 9H) 1.55-1.73 (m, 2H) 1.89-2.17 (m, 3H) 3.41 (br. s., 2H) 3.65 (br. s., 2H) 3.78-3.88 (m, 1H) 3.95 (d, J=8.03 Hz, 1H) 8.34 (d, J=9.03 Hz, 1H) 8.54 (br. s., 1H) 8.61 (dd, J=9.03, 3.01 Hz, 1H) MS m/z 379.1 (M+H)+.

Sources & evidence

ORD record: ord-d13bbd46b4504c4ba4c5c0b21d9f0106
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957074B2

Reaction notes

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