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

HRID 2297793Notes

Reaction equation

HRID 2297793 reaction equation
CN(C)C=O.[C:6]([Cl:11])(=O)[C:7](Cl)=O.[S:12]1[C:20]2C(=O)C=[CH:17][NH:16][C:15]=2[CH:14]=[CH:13]1>C(Cl)Cl>[Cl:11][C:6]1[CH:7]=[CH:17][N:16]=[C:15]2[CH:14]=[CH:13][S:12][C:20]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 5074765Thieno[3,2-b]pyridin-7-ol

Product 1

HCID 112752517-Chlorothieno[3,2-b]pyridineYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 mL round-bottomed flask 100 mL of methylene chloride and dimethylformamide (6.1 mL, 78.6 mmol) were combined and cooled to 0° C. Oxalyl chloride (57 mL, 114 mmol) was added dropwise over several minutes. 4H-Thieno[3,2-b]pyridin-7-one (5.4 g, 35.7 mmol) was added and the solution was heated to reflux. After 2 hours the flask was cooled to room temperature and the resulting solid was filtered and dried in vacuo to afford 6.29 g (100%) of 7-chloro-thieno[3,2-b]pyridine as a yellow solid. 1H NMR (400 MHz, DMSO) d 8.67 (d, 1H), 8.29 (d, 1H), 7.66 (d, 1H), 7.61 (d, 1H); LC-MS: 171 (MH+); HPLC RT: 4.19.

Workup

  1. temperaturethe solution was heated to reflux
  2. temperatureAfter 2 hours the flask was cooled to room temperature
  3. filtrationthe resulting solid was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-18451a9496d949bcb9b223be159bf2d8
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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