2-Bromo-3-nitropyridine → Methyl 3-(4-((3-nitropyridin-2-yl)ethynyl)phenyl)propanoate

HRID 2043004Notes

Reaction equation

HRID 2043004 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[CH:2].Br[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1>>[N+:22]([C:21]1[C:16]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=2)=[N:17][CH:18]=[CH:19][CH:20]=1)([O-:24])=[O:23]

Participants

3

Reactant 2

HCID 5550542-Bromo-3-nitropyridineHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319120Methyl 3-(4-((3-nitropyridin-2-yl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (95 mg, 0.51 mmol) and 2-bromo-3-nitropyridine (113 mg, 0.56 mmol) according to the general procedure IF to give 84 mg (53%) of a red solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:8): Rf=0.16 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 8.84 (dd, J=4.7, 1.6 Hz, 1H), 8.39 (dd, J=8.3, 1.6 Hz, 1H), 7.64-7.59 (m, 2H), 7.44 (dd, J=8.3, 4.7 Hz, 1H), 7.24 (d, J=8.4 Hz, 2H), 3.68 (s, 3H), 2.99 (t, J=7.7 Hz, 2H), 2.65 (t, J=7.7 Hz, 2H); 13C NMR (CDCl3) δ 173.0, 153.5, 146.8, 143.0, 137.6, 132.8, 132.5, 128.6, 122.5, 119.3, 98.0, 85.0, 51.7, 35.2, 30.9; ESI-MS m/z 333.1 (M+Na+).

Sources & evidence

ORD record
ord-e684d109913d47fb9a3df7a0f8d19e44
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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