5-Thiazolecarboxylic acid, 4-methyl-, ethyl ester → 5-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester
Reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[C:13]1[CH:14]=[CH:15][C:16]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[C:17]([CH:20]=1)[C:18]#[N:19]>CS(C)=O.[Pd]>[C:18]([C:17]1[CH:20]=[C:13]([C:4]2[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=2)[CH:14]=[CH:15][C:16]=1[O:21][CH2:22][CH:23]([CH3:25])[CH3:24])#[N:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
To a test tube-type reaction vessel (10 mL) were added ethyl 4-methylthiazole-5-carboxylate (85.5 mg, 0.5 mmol), 5-bromo-2-isobutoxybenzonitrile (127.1 mg, 0.5 mmol) obtained in Reference Example 3, a palladium species, a ligand, a base (1.0 mmol), an additive (0.15 mmol), and a solvent (1.7 mL). Thereafter, the reaction vessel was filled with nitrogen, heated to 120° C. under airtight seal, and the reaction mixture was stirred. After the reaction was complete, a portion of the reaction mixture was diluted with DMSO and the solution obtained was measured by HPLC. The total HPLC area % of the compounds A to D and TM was set as 100% and the calculated yield of the target material was computed from the HPLC area % of the target material. The results are shown in Table 10.
Workup
- customobtained in Reference Example 3
- additionThereafter, the reaction vessel was filled with nitrogen
- customseal
- customthe solution obtained
Sources & evidence
- ORD record
- ord-a199a503892640f897bcaaef58e5cf3d
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952174B2
Reaction notes
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