2-Chloro-4-iodopyridine → Methyl 4-[2-(2-chloro-4-pyridinyl)ethynyl]benzenepropanoate

HRID 2042989Notes

Reaction equation

HRID 2042989 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]=[CH:18][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]=[CH:18][N:17]=1

Participants

3

Reactant 2

HCID 15165112-Chloro-4-iodopyridineHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 54757928Methyl 4-[2-(2-chloro-4-pyridinyl)ethynyl]benzenepropanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (104 mg, 0.55 mmol) and 2-chloro-4-iodopyridine (141 mg, 0.59 mmol) according to the general procedure IC to give 96 mg (58%) of a pale yellow solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:5). Rf: 0.22 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 8.36-8.35 (m, 1H), 7.48-7.45 (m, 2H), 7.42-7.41 (m, 1H), 7.29-7.26 (m, 1H), 7.24-7.21 (m, 2H), 3.67 (s, 3H), 3.01-2.96 (t, 2H, J=7.8 Hz), 2.67-2.62 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 172.9, 151.7, 149.5, 142.4, 134.4, 132.1, 128.6, 125.9, 124.1, 95.4, 85.3, 51.8, 35.2, 30.8; EI-MS calcd for C17H15ClNO2 (M+): 299. found: 299.

Sources & evidence

ORD record
ord-2190f3ef2537416380742be2aefda2fa
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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