Acetone → 2-(5-(7-chlorothieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-2-yl)propan-2-ol
Reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]3[N:17]([CH3:21])[CH:18]=[N:19][CH:20]=3)[S:15][C:8]=12.[CH3:22][C:23]([CH3:25])=[O:24]>O1CCCC1.O>[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]3[N:17]([CH3:21])[C:18]([C:23]([OH:24])([CH3:25])[CH3:22])=[N:19][CH:20]=3)[S:15][C:8]=12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 50 mL round-bottomed flask 7 mL of tetrahydrofuran and n-butyllithium (0.88 mL, 2.5M in hexane) were cooled to −40° C. A suspension of 7-chloro-2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridine (500 mg, 2.00 mmol) in 9 mL of tetrahydrofuran was added dropwise to the solution and stirred for 40 minutes. Acetone (0.79 mL, 3.00 mmol) was added to the anion and the reaction mixture was allowed to warm to room temperature overnight. The mixture was diluted with water and extracted with chloroform (3×50 mL). The combined extracts were dried over NaSO4, filtered, and concentrated. Chromatography on 50 g of silica gel with 5% methanol:methylene chloride afforded 191 mg (31%) of 2-[5-(7-chloro-thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-2-yl]-propan-2-ol. 1H NMR (400 MHz, CDCl3) δ8.58 (d, 1H), 7.51 (s, 1H), 7.28 (d, 1H), 7.24 (s, 1H), 4.02 (s, 3H), 1.77 (s, 6H). LC-MS: 308.1, 310.1 (MH+); HPLC RT: 4.18 min.
Workup
- additionwas added dropwise to the solution
- extractionextracted with chloroform (3×50 mL)
- dry with materialThe combined extracts were dried over NaSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8301c8a2c2b3436fb7c9370f5af4db91
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06492383B1
Reaction notes
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