3-Bromo-4-methylbenzonitrile → 5-(5-Cyano-2-methylphenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide
Reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:24])=[C:11]([NH:13][C:14]([C:16]3[S:20][C:19](B(O)O)=[CH:18][CH:17]=3)=[O:15])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.Br[C:26]1[CH:31]=[C:30]([C:32]#[N:33])[CH:29]=[CH:28][C:27]=1[CH3:34]>>[C:32]([C:30]1[CH:29]=[CH:28][C:27]([CH3:34])=[C:26]([C:19]2[S:20][C:16]([C:14]([NH:13][C:11]3[CH:12]=[C:7]([C:5](=[O:6])[NH:4][CH:1]4[CH2:3][CH2:2]4)[CH:8]=[CH:9][C:10]=3[CH3:24])=[O:15])=[CH:17][CH:18]=2)[CH:31]=1)#[N:33]Participants
3
Procedure
The title compound was prepared by coupling 5-(5-(cyclopropylcarbamoyl)-2-methylphenylcarbamoyl)thiophen-2-ylboronic acid (Example 210, Step A) with commercially available 2-bromo-4-cyanotoluene using the method described in Step B of Example 136 to afford a white solid after purification by reverse phase preparative HPLC (Example 213). HPLC Ret time=3.36 min. LCMS [M+H]+ 416.29.
Workup
- custom