Water → HCID 58382162, compound

HRID 1628081Notes

Reaction equation

HRID 1628081 reaction equation
Cl.[CH3:2][C:3]1[N:7]2[C:8]3[CH:14]=[CH:13][N:12]([S:15]([C:18]4[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=4)(=[O:17])=[O:16])[C:9]=3[N:10]=[CH:11][C:6]2=[CH:5][N:4]=1.C1C(=O)N([Br:32])C(=O)C1.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:32][C:5]1[N:4]=[C:3]([CH3:2])[N:7]2[C:8]3[CH:14]=[CH:13][N:12]([S:15]([C:18]4[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=4)(=[O:16])=[O:17])[C:9]=3[N:10]=[CH:11][C:6]=12

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 67362235HCID 67362235, compound

Product 1

HCID 58382162HCID 58382162, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-methyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride (2.11 g, 5.81 mmol) in DMF (58 ml) was added NBS (1.03 g, 5.81 mmol). The mixture was stirred for about 2 h at rt. The mixture was poured into rapidly stirred water (˜300 mL). Saturated aqueous NaHCO3 (˜15 mL) was added and the mixture stirred for about 1 h. The solid was collected by filtration and washed with water (˜50 mL). The solid was dissolved in DCM (100 mL) and washed with saturated aqueous Na2CO3 (20 mL). The layers were separated and the aqueous layer was extracted with DCM (2×15 mL). The combined organic layers were washed with brine (10 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (80 g Silicycle™ column) eluting with 10% EtOAc in DCM to give 3-bromo-1-methyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (1.62 g, 69%): LCMS (Table 2, Method b) Rt=2.52 min.; MS m/z: 404.96, 406 (M+H)+.

Workup

  1. stirringthe mixture stirred for about 1 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with water (˜50 mL)
  4. dissolutionThe solid was dissolved in DCM (100 mL)
  5. washwashed with saturated aqueous Na2CO3 (20 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with DCM (2×15 mL)
  8. washThe combined organic layers were washed with brine (10 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash column chromatography (80 g Silicycle™ column)
  13. washeluting with 10% EtOAc in DCM

Sources & evidence

ORD record
ord-a19a7a88275a419a886ef899385cc10d
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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