Potassium Carbonate → 6'-Bromo-4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl

HRID 646929Notes

Reaction equation

Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Br:11])[N:3]=1.[CH3:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[Br:11][C:4]1[N:3]=[C:2]([N:16]2[CH2:17][CH2:18][CH:13]([CH3:12])[CH2:14][CH2:15]2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2,6-dibromo-3-nitropyridine (Duffy, J., et al, J. Org. Chem. 56, (9), 3006, (1991)) (282 mg, 1.00 mmol), 4-methylpiperidine (118 μL, 1.00 mmol) and K2CO3 (138 mg, 1.00 mmol) in toluene (10 mL) was heated at 50° C. for 3 h. Toluene was removed in vacuo and the residue obtained was purified on silica (2% EtOAc/hexane) to obtain the title compound (197 mg, 66%). 1H-NMR (CDCl3; 400 MHz): δ 8.32 (d, 1H J=8.2 Hz), 7.94 (d, 1H J=8.2 Hz), 3.82 (m, 2H), 3.04 (m, 2H), 1.85 (m, 3H), 1.3 (m, 2H), 0.99 (d, 3H, J=6.4 Hz).

Workup

customToluene was removed in vacuo
customthe residue obtained
customwas purified on silica (2% EtOAc/hexane)

Sources & evidence

ORD record: ord-d7c6b75165e14b2882048ce936075b39
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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