Isopropanol → HCID 57438775, compound

HRID 2233112Notes

Reaction equation

HRID 2233112 reaction equation
[Na].COC([C:6]1[C:7]2[N:8]([CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[N:14]=2)[CH:9]=[CH:10][N:11]=1)=O.[CH3:22][CH:23]([OH:25])[CH3:24]>>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[N:14]=[C:7]3[C:6]([O:25][CH:23]([CH3:24])[CH3:22])=[N:11][CH:10]=[CH:9][N:8]3[CH:12]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 5360545Sodium2×HCID 57438736Methyl 2-(4-fluorophenyl)imidazo[1,2-a]pyrazine-8-carboxylate

Product 1

HCID 57438775HCID 57438775, compoundYield 70%

Procedure

A mixture of anhydrous IPA (25 mL) and sodium (0.4 g, 17.4 mmol) was heated at reflux until the sodium was consumed. The reaction mixture was cooled to ambient temperature and the 8-chloro-2-(4-fluorophenyl)-imidazo[1,2-a]pyrazine (prepared from general procedure B using 3-chloropyrazin-2-ylamine and 2-bromo-1-(4-fluorophenyl)-ethanone; 2.0 g, 8 mmol) was added. The reaction mixture was heated at reflux for about 2 h, cooled to ambient temperature, and partitioned between EtOAc and water. The layers were separated and the organic phase was dried over MgSO4, filtered, and evaporated. The resulting solid was triturated with heptane to afford 1.52 g (70%) of the title compound: LC/MS (Table 1, Method g) Rt=2.78 min; MS m/z: 272.2 (M+H)+.

Workup

  1. temperaturewas heated
  2. customwas consumed
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for about 2 h
  5. temperaturecooled to ambient temperature
  6. custompartitioned between EtOAc and water
  7. customThe layers were separated
  8. dry with materialthe organic phase was dried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe resulting solid was triturated with heptane

Sources & evidence

ORD record
ord-2c9c53c8ad104527930f290aff01efce
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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