2-Amino-3-chloropyridine → N-(3-chloropyridin-2-yl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide
Reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][Si](C)(C)N[Si](C)(C)C.[Na].[S:19]1[C:23]2[C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[O:26][CH2:27][CH2:28][C:22]=2[CH:21]=[C:20]1[C:33](Cl)=[O:34]>C1COCC1>[Cl:8][C:7]1[C:2]([N:1]([CH3:9])[C:33]([C:20]2[S:19][C:23]3[C:24]4[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=4[O:26][CH2:27][CH2:28][C:22]=3[CH:21]=2)=[O:34])=[N:3][CH:4]=[CH:5][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
An ice water cooled solution of 2-amino-3-chloropyridine (0.200 g, 0.755 mmol) in tetrahydrofuran (1.5 mL, 18 mmol) was reacted with a THF solution of 1 M sodium hexamethyldisilazane to give a clear solution. This reaction mix was stirred at cooled temperature for 30 minutes. Next, 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchloride (0.100 g, 0.378 mmol) was added portionwise as a solid. Reaction mix was stirred at room temperature with monitor for formation of desired product and concentrated in vacuo to a solid residue. This residue was taken into ethyl acetate and the organic was washed with water, then saline and dried (Na2SO4). The crude material was purified by MPLC on silica, eluting with 10% to 80% ethyl acetate/hexanes to give 128 mg N-(3-chloropyridin-2-yl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide, 34% of theoretical yield.
Workup
- customto give a clear solution
- additionThis reaction mix
- temperatureat cooled temperature for 30 minutes
- customReaction
- additionmix
Sources & evidence
- ORD record
- ord-a0297cfa7d9446279a47ad1396846bbb
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928248B2
Reaction notes
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