4-Bromopyridinium chloride → HCID 54757837, compound

HRID 2043013Notes

Reaction equation

HRID 2043013 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].Cl.Br[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>>[N:20]1[CH:21]=[CH:22][C:17]([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)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 881004-Bromopyridinium chlorideHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 54757837HCID 54757837, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (94 mg, 0.50 mmol) and 4-bromopyridine hydrochloride (108 mg, 0.55 mmol) according to the general procedure IC to give 72 mg (54%) of a white solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:5). Rf=0.26 (EtOAc:PE, 1:1); 1H NMR (CDCl3) δ 8.52 (dd, J=4.5, 1.5 Hz, 2H), 7.45-7.39 (m, 2H), 7.29 (dd, J=4.5, 1.6 Hz, 2H), 7.14 (d, J=8.3 Hz, 2H), 3.60 (s, 3H), 2.90 (t, J=7.7 Hz, 2H), 2.57 (t, J=7.7 Hz, 2H); 13C NMR (CDCl3) δ 172.0, 148.8, 141.0, 131.0, 130.5, 127.5, 124.5, 119.0, 92.9, 85.5, 50.7, 34.3, 29.8; ESI-MS m/z 288.1 (M+Na+).

Sources & evidence

ORD record
ord-3785fc5cac22422888b00a443c716db3
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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