Hydrochloric Acid → HCID 71735040, compound

HRID 1485009Notes

Reaction equation

HRID 1485009 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:14]=[CH:13][CH:12]=[C:11]3[N:15]=[C:16](SC)[N:17]=[C:10]23)=[CH:4][CH:3]=1.[ClH:20]>>[Cl:20][C:16]1[N:17]=[C:10]2[N:9]([CH2:8][C:5]3[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:14]=[CH:13][CH:12]=[C:11]2[N:15]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 89826351HCID 89826351, compound

Product 1

HCID 71735040HCID 71735040, compoundYield 58%

Conditions

Temperature
-10 °C

Procedure

A solution of 4-[(6-chloro-3-pyridyl)methyl]-2-methylsulfanyl-imidazo[4,5-b]pyridine (2.22 g, 7.63 mmol) in 25 mL concentrated aqueous hydrochloric acid was cooled to −10° C. and gaseous Cl2 was bubbled through the solution for 1 h. The mixture was stirred at −10° C. for additional 2 h and for 12 h at room temperature. Afterwards the reaction mixture was poured into ice-water, basified to pH 4-5 with NaOH solution (15% in H2O) and extracted three times with CH2Cl2. The combined organic extracts were washed with water, dried with Na2SO4 and the solvent was removed under reduced pressure. Purification by flash column chromatography (SiO2, gradient of MeOH/CH2C12) yielded 1.23 g (4.43 mmol, 58%) of compound E1.8.

Workup

  1. customgaseous Cl2 was bubbled through the solution for 1 h
  2. additionAfterwards the reaction mixture was poured into ice-water
  3. extractionextracted three times with CH2Cl2
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried with Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customPurification by flash column chromatography (SiO2, gradient of MeOH/CH2C12)

Sources & evidence

ORD record
ord-436415c5c0534abbb4f24acdde7a89b1
Source dataset
uspto-grants-2016_08
Patent number
US09422280B2

Reaction notes

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