Phosphorus oxychloride → 2-Bromo-4-chlorothieno[3,2-c]pyridine-7-carbonitrile

HRID 1868332Notes

Reaction equation

HRID 1868332 reaction equation
[C:1]([C:3]1[C:4]2[S:12][C:11]([Br:13])=[CH:10][C:5]=2[C:6](=O)[NH:7][CH:8]=1)#[N:2].P(Cl)(Cl)([Cl:16])=O>>[Br:13][C:11]1[S:12][C:4]2[C:3]([C:1]#[N:2])=[CH:8][N:7]=[C:6]([Cl:16])[C:5]=2[CH:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 184465192-Bromo-4-oxo-4,5-dihydrothieno[3,2-c]pyridine-7-carbonitrile

Product 1

HCID 184465172-Bromo-4-chlorothieno[3,2-c]pyridine-7-carbonitrile

Procedure

2-Bromo-7-cyano-4-oxo-4,5-dihydrothieno[3,2-c]-pyridine (99) (2.0 g, 7.84 mmol) was dissolved in phosphorus oxychloride (60 mL) and the resulting solution heated at reflux for 2 h. After this time the mixture was poured into ice and stirred for 1 h. The precipitated solid was filtered, washed with water and dried (50° C., P2O5, in vacuo), affording a brown solid (1.99 g). 1H NMR (300 MHz, d6-DMSO) δ 9.05 (s, 1H), 8.21 (s, 1H)

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 2 h
  3. additionAfter this time the mixture was poured into ice
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water
  6. dry with materialdried (50° C., P2O5, in vacuo)

Sources & evidence

ORD record
ord-dee2e0cc61e942c5bb45681e37ef9c47
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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