2,6-Dichloro-4-iodopyridine → Methyl 3-(4-((2,6-dichloropyridin-4-yl)ethynyl)phenyl)propanoate

HRID 2043003Notes

Reaction equation

HRID 2043003 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:15][C:16]1[CH:21]=[C:20](I)[CH:19]=[C:18]([Cl:23])[N:17]=1>>[Cl:15][C:16]1[CH:21]=[C:20]([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:19]=[C:18]([Cl:23])[N:17]=1

Participants

3

Reactant 2

HCID 117373932,6-Dichloro-4-iodopyridineHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 45112387Methyl 3-(4-((2,6-dichloropyridin-4-yl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (98 mg, 0.52 mmol) and 2,6-dichloro-4-iodopyridine (152 mg, 0.56 mmol) according to the general procedure IF to give 95 mg (55%) of a pale yellow solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:7): Rf=0.11 (EtOAc:PE, 1:7); 1H NMR (CDCl3) δ 7.46 (d, J=8.3 Hz, 2H), 7.34 (s, 1H), 7.22 (s, 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, 150.7, 142.0, 132.7, 132.3, 128.7, 128.5, 124.4, 119.8, 81.4, 73.8, 51.7, 35.2, 30.9; ESI-MS m/z 356.0 (M+Na+).

Sources & evidence

ORD record
ord-6aebe5baba704bc6bb332381bb0ac5e1
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

Loading…