N-bromobutanimide → HCID 58382107, compound

HRID 1628088Notes

Reaction equation

HRID 1628088 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH2:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]3[CH:22]=[N:21][N:20]([CH3:23])[C:18]3=2)[N:13]([S:24]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:12]=1)[CH3:10]>C1COCC1.[O-]S([O-])(=S)=O.[Na+].[Na+]>[Br:8][C:22]1[C:17]2[C:18](=[C:19]3[C:11]([CH2:9][CH3:10])=[CH:12][N:13]([S:24]([C:27]4[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=4)(=[O:26])=[O:25])[C:14]3=[N:15][CH:16]=2)[N:20]([CH3:23])[N:21]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimide4×HCID 58382318HCID 58382318, compound

Product 1

HCID 58382107HCID 58382107, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

NBS (0.708 g, 3.98 mmol) was added to a solution of 8-ethyl-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (1.41 g, 3.98 mmol, Preparation #2, Step F) in THF (60 mL). The mixture was allowed to stir at rt. After 16 h additional NBS (0.106 g, 0.597 mmol) was added and reaction was stirred for about 3 h, then another portion of NBS (0.142 g, 0.796 mmol) was added. After another 1 h three equal portions of NBS (0.213 g, 1.19 mmol) were added over about 6 h. The mixture was then diluted with saturated aqueous Na2S2O3 (50 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was suspended in Et2O (10 mL) and sonicated for about 3 min. The precipitate was collected by filtration, washed with Et2O (10 mL) and dried in a vacuum oven at about 60° C. for about 3 h to give 3-bromo-8-ethyl-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (1.3 g, 75%): LC/MS (Table 2, Method c) Rt=1.58 min.; MS m/z: 433 (M+H)+.

Workup

  1. customreaction
  2. stirringwas stirred for about 3 h
  3. extractionextracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customsonicated for about 3 min
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with Et2O (10 mL)
  10. customdried in a vacuum oven at about 60° C. for about 3 h

Sources & evidence

ORD record
ord-3634fb1a0d644a188374a9ea0d43b63b
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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