Pyridine → 2-(2,6-Dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine

HRID 2366316Notes

Reaction equation

HRID 2366316 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4](Cl)=[N:5][C:6]1[C:11]([F:12])=[CH:10][N:9]=[CH:8][C:7]=1F.NC(N)=[S:23].N1C=CC=CC=1.CCN(CC)CC>C(O)(C)C>[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4]1[S:23][C:7]2[CH:8]=[N:9][CH:10]=[C:11]([F:12])[C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2723790ThioureaHCID 866690292,6-dichloro-N-(3,5-difluoropyridin-4-yl)-4-iodobenzimidoyl chloride

Product 1

HCID 668015632-(2,6-Dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridineYield 66%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 2,6-dichloro-N-(3,5-difluoropyridin-4-yl)-4-iodobenzimidoyl chloride (8.8 g, 19.7 mmol), thiourea (6.0 g, 78.8 mol) and pyridine (5.4 mL, 66.9 mmol) in isopropanol (80 mL), under a nitrogen atmosphere, was heated under reflux for 6 hours. After this time, the reaction mixture was cooled to 70° C. and Et3N (16.4 mL, 118.1 mmol) was added over 5 minutes and then the resultant mixture was heated under reflux for a further 18 hours. Upon cooling to room temperature, the precipitate obtained was collected by filtration and the filtrate was then partitioned between water and EtOAc. The aqueous phase was further extracted with EtOAc (×2) and the combined organic layers were dried (MgSO4), filtered and concentrated to dryness to afford the title compound as an off-white solid (5.5 g, 66% yield). LCMS (Method D): RT=4.22 min, m/z: 426 [M+H+].

Workup

  1. temperatureunder a nitrogen atmosphere, was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureunder reflux for a further 18 hours
  4. temperatureUpon cooling to room temperature
  5. customthe precipitate obtained
  6. filtrationwas collected by filtration
  7. customthe filtrate was then partitioned between water and EtOAc
  8. extractionThe aqueous phase was further extracted with EtOAc (×2)
  9. dry with materialthe combined organic layers were dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cee47e67de3a46bf9d8d61e25ba7ef1a
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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