Hydrochloric Acid → 3-(4-Pyridyl)-2-(4-fluorophenyl)-4,7-diaza-indole

HRID 395958Notes

Reaction equation

HRID 395958 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9](O[Si](C(C)(C)C)(C)C)[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1.Cl>O>[N:13]1[CH:12]=[CH:11][C:10]([C:9]2[C:31]3[C:26](=[N:27][CH:28]=[CH:29][N:30]=3)[NH:25][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 78747AminopyrazineHCID 10991586HCID 10991586, compound

Product 1

HCID 181752253-(4-Pyridyl)-2-(4-fluorophenyl)-4,7-diaza-indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

1-(4-Fluorophenyl)-2-t-butyldimethylsiloxy-2-(4-pyridyl)ethanone (16) (5.44 g, 15.77 mmol), 2-aminopyrazine (1.00 g, 10.5 mmol), and concentrated HCl (30 mL) were heated in a sealed tube to 190° C. behind an explosion shield. After 3 h at 190° C., the reaction was allowed to cool to 23° C. then diluted with water (100 mL). After further dilution with concentrated ammonium hydroxide to pH of 12, the reaction was extracted with methylene chloride (3×200 mL), and dried (MgSO4). After concentration in vacuo, the residue was purified by applying flash chromatography (100% ethyl acetate) to afford 3-(4-pyridyl)-2-(4-fluorophenyl)-4,7-diaza-indole (62): Mass Spectrum (CI) 291 (MH+).

Workup

  1. extractionAfter further dilution with concentrated ammonium hydroxide to pH of 12, the reaction was extracted with methylene chloride (3×200 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified

Sources & evidence

ORD record
ord-c22f4532f7db47dea0ccd9cfb87e0a92
Source dataset
uspto-grants-2003_08
Patent number
US06605634B2

Reaction notes

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