2-Iodopyridine → Methyl 3-(4-(pyridin-2-ylethynyl)phenyl)propanoate

HRID 2042987Notes

Reaction equation

HRID 2042987 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][CH:19]=[CH:18][N:17]=1>>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:2]#[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

Participants

3

Reactant 2

HCID 2211262-IodopyridineHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 54757832Methyl 3-(4-(pyridin-2-ylethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (99 mg, 0.52 mmol) and 2-iodopyridine (0.07 mL, 0.66 mmol) according to the general procedure IC to give 69 mg (50%) of a pale yellow solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:3). Rf: 0.09 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 8.62-8.60 (m, 1H), 7.70-7.64 (m, 1H), 7.54-7.49 (m, 3H), 7.25-7.18 (m, 3H), 3.67 (s, 3H), 2.99-2.94 (t, 2H, J=7.8 Hz), 2.67-2.61 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.0, 150.0, 143.5, 141.6, 136.1, 132.2, 128.4, 127.1, 122.6, 120.2, 89.2, 88.4, 51.6, 35.2, 30.8; EI-MS calcd for C17H15NO2 (M+): 265. found: 265.

Sources & evidence

ORD record
ord-d81a7c0871524ff4adaad92d6b7d58e7
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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