7-Chloro-4-iodoquinoline → HCID 54758023, compound

HRID 2042996Notes

Reaction equation

HRID 2042996 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:25]=[C:24]2[C:19]([C:20](I)=[CH:21][CH:22]=[N:23]2)=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([C:2]#[C:1][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=3)=[CH:21][CH:22]=[N:23]2)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 111853697-Chloro-4-iodoquinolineHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 54758023HCID 54758023, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (54 mg, 0.29 mmol) and 7-chloro-4-iodoquinoline (93 mg, 0.32 mmol) according to the general procedure IC to give 54 mg (54%) of a beige solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:4). Rf=0.06 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 8.88 (d, J=4.8 Hz, 1H), 8.27 (d, J=9.0 Hz, 1H), 8.11 (m, 1H), 7.59-7.52 (m, 4H), 7.28-7.25 (m, 2H), 3.69 (s, 3H), 3.01 (t, J=7.8 Hz, 2H), 2.67 (t, J=7.8 Hz, 2H); 13C NMR (CDCl3) δ 172.9, 150.8, 148.5, 142.4, 135.8, 132.1, 129.9, 128.8, 128.6, 128.1, 127.4, 126.1, 123.5, 119.9, 99.2, 84.4, 51.7, 35.2, 30.9; ESI-MS m/z 372.1 (M+Na+).

Sources & evidence

ORD record
ord-1758b3d3502b4c468cbd7c6d6be05204
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

Loading…