Oxalyl chloride → 2-(Azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O-:13])=O)[S:10][C:3]=12.[Li+].C(Cl)(=O)C(Cl)=O.Cl.[NH:22]1[CH2:25][CH2:24][CH2:23]1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[N:22]1([C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:8]=2)=[O:13])[CH2:25][CH2:24][CH2:23]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A 50 mL round bottom flask was charged with lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate (0.500 g, 2.28 mmol), methylene chloride (15 ml), and 12 drops of DMF. Oxalyl chloride (0.298 ml, 3.42 mmol) was added dropwise, and the mixture was stirred at room temperature for 3 hours and concentrated to yield a tan solid. This was redissolved in methylene chloride (15 ml). Azetidine hydrochloride (0.426 g, 4.55 mmol) was added in one portion and Hunig's Base (1.59 ml, 9.11 mmol) was added dropwise. This mixture was stirred at room temperature overnight, then diluted with methylene chloride (15 mL) and washed with water (25 mL), sat. NaHCO3 (25 mL), and brine (25 mL). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo to yield azetidin-1-yl(7-chlorothieno[3,2-b]pyridin-2-yl)methanone (0.58 g, 100% yield) as a tan solid.
Workup
- concentrationconcentrated
- customto yield a tan solid
- additionwas added dropwise
- stirringThis mixture was stirred at room temperature overnight
- washwashed with water (25 mL), sat. NaHCO3 (25 mL), and brine (25 mL)
- dry with materialThe organic layer was dried with MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-4b8ebae095054f1e85807f5a7912756f
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088794B2
Reaction notes
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