Iodine → HCID 66734093, compound

HRID 1929705Notes

Reaction equation

HRID 1929705 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16](I)=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].II>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][CH:16]=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([Br:28])=[CH:26][CH:27]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 807IodineHCID 66733873HCID 66733873, compound

Product 1

HCID 66734093HCID 66734093, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (−30° C.) solution of 8-[2-(4-bromo-phenyl)-ethyl]-3-ethyl-1-iodo-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (2.200 g; 3.927 mmol) in anhydrous THF (90 ml) was treated dropwise with a solution of 1-Methylmagnesium bromide in THF (10.25 ml; 10.25 mmol; 2.6 eq.) until complete removal of the iodine substituent. The mixture was then quenched with water (5 ml), diluted with ether (100 ml), and was allowed to warm-up to rt. This solution was washed with brine (2×150 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM/MeOH=15/1) to give the pure product 8-[2-(4-bromo-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow oil (1.570 g; 92%). LC-MS: tR=0.93 min.; [M+H]+=435.98 g/mol.

Workup

  1. customThe mixture was then quenched with water (5 ml)
  2. additiondiluted with ether (100 ml)
  3. washThis solution was washed with brine (2×150 ml)
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe crude was purified by FC (DCM/MeOH=15/1)

Sources & evidence

ORD record
ord-f9a63c7521f44596bbf09a8c88a52ddf
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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