1-Chloro-2-ethynyl-4-(trifluoromethyl)benzene → 3-[2-Chloro-5-(trifluoromethyl)phenyl]-1-(7-methoxyquinolin-3-yl)prop-2-yn-1-one

HRID 1865436Notes

Reaction equation

HRID 1865436 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]#[CH:13].CON(C)[C:17]([C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[C:24]([O:29][CH3:30])[CH:23]=2)=[O:18]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=1[C:12]#[C:13][C:17]([C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[C:24]([O:29][CH3:30])[CH:23]=2)=[O:18]

Participants

3

Reactant 2

HCID 117457731-Chloro-2-ethynyl-4-(trifluoromethyl)benzeneHCID 86094167HCID 86094167, compound2×

Product 1

HCID 685697303-[2-Chloro-5-(trifluoromethyl)phenyl]-1-(7-methoxyquinolin-3-yl)prop-2-yn-1-one

Procedure

The title compound was prepared with the alkyne from step B and N,7-dimethoxy-N-methylquinoline-3-carboxamide the intermediate from example 2 step E following the procedure described in example 2 step F. 1H NMR (CDCl3, 500 MHz): 9.62 (d, J=2.1 Hz, 1H), 8.97 (d, J=2.1 Hz, 1H), 8.03 (s, 1H), 7.87 (d, J=8.9 Hz, 1H), 7.69 (d, J=3.0 Hz, 2H), 7.51 (d, J=2.3 Hz, 1H), 7.31 (dd, J=2.3, 8.9 Hz, 1H), 4.03 (s, 3H). LC-MS: 3.85 min. (M+H)=389.9.

Workup

  1. custom3.85 min. (M+H)=389.9

Sources & evidence

ORD record
ord-00e1a4f58af0446098a06cdd2687e0c5
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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