N-bromobutanimide → HCID 76849734, compound

HRID 448983Notes

Reaction equation

HRID 448983 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([I:11])=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.C1C(=O)N([Br:19])C(=O)C1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:19][C:10]1[N:9]=[C:8]([I:11])[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]=12

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 76849761HCID 76849761, compound

Product 1

HCID 76849734HCID 76849734, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 8-chloro-3-iodo-imidazo[1,5-a]pyrazine (730.0 mg, 2.61 mmol) in DMF (8.00 mL) was added NBS (557.9 mg, 3.13 mol) in 3 portions at 0° C. The resulting mixture was allowed to warm up to rt. and stirred at rt. for 2 hours. To the mixture was added 30 mL saturated NaHCO3 aq. solution, extracted with DCM (20 mL×3). Organic phase was combined and dried (Na2SO4) and evaporated to give crude material which was used in next step without further purification. 1H NMR (400 MHz, MeOD) δ 7.48 (d, J=5.1 Hz, 1H) 8.02 (d, J=5.1 Hz, 1H). MS (ES: m/z: 357.68, 359.67, 361.68 [MH+]. HPLC: tR=3.22 min (OpenLynx: polar—5 min).

Workup

  1. extractionextracted with DCM (20 mL×3)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto give crude material which
  5. customwas used in next step without further purification
  6. customHPLC: tR=3.22 min (OpenLynx: polar—5 min)

Sources & evidence

ORD record
ord-20c8ce532e7842988dec5a011e10c14c
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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