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

HRID 2043006Notes

Reaction equation

HRID 2043006 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH:10]2[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1)#[CH:2].[Cl:16][C:17]1[CH:22]=[C:21](I)[CH:20]=[C:19]([Cl:24])[N:18]=1>>[Cl:16][C:17]1[CH:22]=[C:21]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH:9]3[CH2:11][CH:10]3[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=2)[CH:20]=[C:19]([Cl:24])[N:18]=1

Participants

3

Reactant 2

HCID 117373932,6-Dichloro-4-iodopyridineHCID 58319131Methyl 2-(4-ethynylphenyl)cyclopropanecarboxylate

Product 1

HCID 58319084Methyl 2-(4-((2,6-dichloropyridin-4-yl)ethynyl)phenyl)cyclopropanecarboxylate

Procedure

The title compound was prepared from methyl 2-(4-ethynylphenyl)cyclopropanecarboxylate (80 mg, 0.40 mmol) and 2,6-dichloro-4-iodopyridine (121 mg, 0.44 mmol) according to the general procedure IF to give 19 mg (23%) of a white solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:10): Rf=0.36 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.45 (d, J=8.2 Hz, 2H), 7.34 (s, 2H), 7.11 (d, J=8.2 Hz, 2H), 3.73 (s, 3H), 2.61-2.48 (m, 1H), 2.02-1.90 (m, 1H), 1.67 (dt, J=10.0, 5.1 Hz, 1H), 1.35 (ddd, J=8.4, 6.4, 4.8 Hz, 1H); 13C NMR (CDCl3) δ 173.4, 150.7, 142.5, 136.5, 132.2, 126.4, 124.4, 119.2, 96.7, 84.7, 52.1, 26.1, 24.4, 17.3; ESI-MS m/z 368.1 (M+Na+).

Sources & evidence

ORD record
ord-b9c29526fcf045c08ca9a9bba100d698
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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