Diethyl Ether → HCID 57438749, compound

HRID 2233097Notes

Reaction equation

HRID 2233097 reaction equation
C[Mg+].[Br-].CCO[CH2:7][CH3:8].ClC1[C:11]2[N:12]([CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:18]=2)[CH:13]=[CH:14][N:15]=1.C1COCC1>CN1C(=O)CCC1>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[N:18]=[C:11]3[C:7]([CH3:8])=[N:15][CH:14]=[CH:13][N:12]3[CH:16]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8028TetrahydrofuranHCID 574387418-Chloro-2-(4-fluorophenyl)imidazo[1,2-A]pyrazineHCID 178418689HCID 178418689, compound2×

Product 1

HCID 57438749HCID 57438749, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3M MeMgBr in Et2O (16.1 mL, 48.3 mmol) was added drop-wise to a mixture of 8-chloro-2-(4-fluorophenyl)-imidazo[1,2-a]pyrazine (10.0 g, 40.6 mmol), ferric acetylacetonate (0.71 g, 2.0 mmol), THF (240 mL), and NMP (23 mL) at about 0° C. The mixture was warmed to ambient temperature over about 1 hour. After about 1 hour, the reaction was cooled to about 0° C. and treated with additional 3M MeMgBr in Et2O (4 mL, 12 mmol). The mixture was allowed to warm to ambient temperature over about 1 h. After about an additional 1 h, the mixture was quenched with water and extracted with EtOAc. The organic layers were combined and dried with Na2SO4. After concentration, the crude material was purified by FCC on silica gel using EtOAc as an eluent to afford the expected product as an off-white solid (9.6 g, 100%): LC/MS (Table 1, Method b) Rt=1.8 min; MS m/z: 228.2 (M+H)+.

Workup

  1. temperaturethe reaction was cooled to about 0° C.
  2. temperatureto warm to ambient temperature over about 1 h
  3. waitAfter about an additional 1 h
  4. customthe mixture was quenched with water
  5. extractionextracted with EtOAc
  6. dry with materialdried with Na2SO4
  7. concentrationAfter concentration
  8. customthe crude material was purified by FCC on silica gel

Sources & evidence

ORD record
ord-2cb318c1ac994699bf3fb96fb737e060
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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