N-bromobutanimide → 3-Bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

HRID 1969630Notes

Reaction equation

HRID 1969630 reaction equation
[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][N:16]([S:19]([C:22]5[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=5)(=[O:21])=[O:20])[C:13]=4[N:14]=[CH:15][C:10]3=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:36])C(=O)C1>C1COCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Br:36][C:9]1[N:8]=[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[N:11]2[C:12]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:20])=[O:21])[C:13]=3[N:14]=[CH:15][C:10]=12

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 580099171-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

Product 1

HCID 583822553-Bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazineYield 85.1%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.27 g, 0.67 mmol, prepared using Q from Preparation #13, Lawesson's reagent, and mercury(II) acetate) in THF (10 mL) at about 0° C. was added a solution of NBS (0.12 g, 0.672 mmol) in THF (2 mL). After about 30 min, the reaction mixture was diluted with EtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL). The organic layer was separated, concd in vacuo, and purified by chromatography on silica gel (40 g) eluting with EtOAc:DCM:heptane (1:1:2) to provide 3-bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.27 g 83%) as a tan solid: LC/MS (Table 1, Method a) Rt=3.12 min; MS m/z 473, 475 (1:1) (M+H)+.

Workup

  1. customThe organic layer was separated
  2. customconcd in vacuo, and purified by chromatography on silica gel (40 g)
  3. washeluting with EtOAc:DCM:heptane (1:1:2)

Sources & evidence

ORD record
ord-8d30041b43334f3b84430ec9ef7b1dd0
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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