Phosphorus oxychloride → 7-Chloro-6-nitrothieno[3,2-b]pyridine

HRID 1499408Notes

Reaction equation

HRID 1499408 reaction equation
O=P(Cl)(Cl)[Cl:3].[N+:6]([C:9]1[C:10](O)=[C:11]2[S:17][CH:16]=[CH:15][C:12]2=[N:13][CH:14]=1)([O-:8])=[O:7]>>[Cl:3][C:10]1[C:9]([N+:6]([O-:8])=[O:7])=[CH:14][N:13]=[C:12]2[CH:15]=[CH:16][S:17][C:11]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526786HCID 178526786, compound

Product 1

HCID 142079507-Chloro-6-nitrothieno[3,2-b]pyridineYield 82%

Conditions

Temperature
110 °C

Procedure

POCl3 (20.0 mL) was added to 6-nitrothieno[3,2-b]pyridin-7-ol (1.56 g, 7.95 mmol). The mixture was stirred at 110° C. for 3 h. The reaction mixture was then concentrated under reduced pressure. The resulting residue was dissolved in DCM (150 mL), and a saturated aq. NaHCO3 (150 mL) was added slowly. The organic layer was washed with water (100 mL) and brine (100 mL), then dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0 to 30% EtOAc in hexanes) to afford the sub-title compound as a pale yellow solid (1.39 g, 82%). LCMS calc. for C2H4ClN2O2S (M+H)+: m/z=215.0. found 215.0.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in DCM (150 mL)
  3. additiona saturated aq. NaHCO3 (150 mL) was added slowly
  4. washThe organic layer was washed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (0 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-eab9de10bae8401db1f0c174a760e6dc
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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