Dimethylformamide → 7-Chlorothieno[3,2-b]pyridine-2-carboxamide

HRID 1063136Notes

Reaction equation

HRID 1063136 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+].S(Cl)(Cl)=O.C(Cl)Cl.C[N:23](C=O)C>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([NH2:23])=[O:13])[S:10][C:3]=12

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 594272817-Chlorothieno[3,2-b]pyridine-2-carboxamideYield 100%

Procedure

A solution of lithium 7-chloro-thieno[3,2-b]pyridine-2-carboxylate (1.0 g, 4.7 mmol), thionyl chloride (7.0 mmol, 3.5 mL), CH2Cl2 (40 mL), and DMF (0.4 mL) was heated to reflux. After 3 h the resulting yellow solution was concentrated under reduced pressure, the resulting residue was suspended in CH2Cl2 (60 mL), and NH3 gas was bubbled through the mixture for 10 min. The reaction mixture was filtered to give the title compound as a white solid (1.17 g, 100%). MS: 213.0/215.1 (MH+); HPLC Rf: 3.44 min; HPLC purity: 98%.

Workup

  1. concentrationAfter 3 h the resulting yellow solution was concentrated under reduced pressure
  2. customNH3 gas was bubbled through the mixture for 10 min
  3. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-3763133b7c0a4b97a245ec79a573e7dd
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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