Hydrochloric Acid → HCID 68615965, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:16]=1)[CH2:7][O:8][Si](C(C)(C)C)(C)C.C([Mg]Cl)(C)C.[CH:23]1[N:24]=[CH:25][N:26]2[CH2:31][CH2:30][CH2:29][C:28](=[O:32])[C:27]=12.Cl>O1CCCC1.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]2([OH:32])[CH2:29][CH2:30][CH2:31][N:26]3[CH:25]=[N:24][CH:23]=[C:27]23)=[C:6]([CH2:7][OH:8])[CH:16]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 6.55 mmol of (5-bromo-2-iodo-benzyloxy)-tert-butyl-dimethyl-silane in 20 ml of tetrahydrofuran is cooled to −20° C. 6.55 mmol of an isopropymagnesium chloride solution (2M in tetrahydrofuran) is added dropwise and stirring continued for 1 h at −20° C. A solution of 4.37 mmol of 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one [426219-51-4] in 40 ml of tetrahydrofuran is added dropwise and the reaction mixture stirred for 40 minutes at −20° C. The reaction mixture is poured into a mixture of 0.1N aqueous HCl and dichloromethane and the layers are separated. The aqueous layer is basified with sodium bicarbonate and extracted with ethyl acetate. The combined organic layers are dried over sodium sulfate, filtered and concentrated under reduced pressure. The title compound is obtained as a white foam and used for the next step without further purification. Rt=4.61 (gradient II).
Workup
- stirringthe reaction mixture stirred for 40 minutes at −20° C
- customthe layers are separated
- extractionextracted with ethyl acetate
- dry with materialThe combined organic layers are dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ee859687df7943028844e15275268c41
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324235B2
Reaction notes
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