Hydrochloric Acid → 7-chloro-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridine

HRID 2297826Notes

Reaction equation

HRID 2297826 reaction equation
C([Si](C)(C)[C:6]1[N:10]([CH3:11])[C:9]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[Cl:21])[CH:13]=2)=[CH:8][N:7]=1)(C)(C)C.Cl>CO.O>[Cl:21][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:13]=[C:12]([C:9]3[N:10]([CH3:11])[CH:6]=[N:7][CH:8]=3)[S:20][C:19]=12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 183829312-[2-(tert-Butyl-dimethyl-silanyl)-3-methyl-3H-imidazol-4-yl]-7-chloro-thieno[3,2-b]pyridine

Product 1

HCID 222500727-chloro-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridineYield 84.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-[2-(tert-Butyl-dimethyl-silanyl)-3-methyl-3H-imidazol-4-yl]-7-chloro-thieno[3,2-b]pyridine (912 mg, 2.50 mmol) was dissolved in 15 mL of methanol and 10 mL of 1N aqueous hydrochloric acid and heated to 35° C. overnight. The solution was cooled, diluted with water, and extracted with ethyl acetate (3×30 mL). The aqueous layer was made basic (pH 9) with 1N aqueous sodium hydroxide and extracted with chloroform (3×30 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated to afford 528 mg (84%) of 7-chloro-2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridine. 1H NMR (400 MHz, CD3OD) δ8.58 (d, 1H), 7.84 (s, 1H), 7.68 (s, 1H), 7.47 (d, 1H), 7.42 (s, 1H), 3.93 (s, 3H). LC-MS: 250.1, 252 (MH+); HPLC RT: 4.40 min.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. extractionextracted with chloroform (3×30 mL)
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea391a8901d1429db4a1488bad838f0a
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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