4-Iodo-2-methylpyridine → Methyl 3-(4-((2-methylpyridin-4-yl)ethynyl)phenyl)propanoate

HRID 2043002Notes

Reaction equation

HRID 2043002 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].I[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[CH:17]=1>>[CH3:22][C:18]1[CH:17]=[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)[CH:21]=[CH:20][N:19]=1

Participants

3

Reactant 2

HCID 126913224-Iodo-2-methylpyridineHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 54757926Methyl 3-(4-((2-methylpyridin-4-yl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (95 mg, 0.50 mmol) and 4-iodo-2-methylpyridine (0.07 mL, 0.59 mmol) according to the general procedure IF to give 62 mg (44%) of a pale yellow solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:5): Rf=0.50 (EtOAc:PE, 1:2); 1H NMR (CDCl3) δ 8.48-8.46 (m, 1H), 7.48-7.45 (m, 2H), 7.25-7.20 (m, 4H), 3.67 (s, 3H), 2.98 (t, J=7.8 Hz, 2H), 2.64 (t, J=7.8 Hz, 2H), 2.56 (s, 3H); 13C NMR (CDCl3) δ 173.1, 158.6, 149.3, 142.0, 132.1, 131.8, 128.6, 125.1, 122.7, 120.3, 93.4, 86.9, 51.8, 35.4, 31.0, 24.5; ESI-MS m/z 302.1 (M+Na+).

Sources & evidence

ORD record
ord-d498bc381b5e4f7e80e46dbc64cc86ae
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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