Boron tribromide → 4-(7,7-Dimethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-yl)phenol
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][N:11]3[CH:17]=[N:18][CH:19]=[C:10]23)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[CH3:15][C:14]1([CH3:16])[CH2:13][CH2:12][N:11]2[CH:17]=[N:18][CH:19]=[C:10]2[CH:9]1[C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 3.30 mmol of 8-(4-methoxyphenyl)-7,7-dimethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 50 ml of dichloromethane is admixed dropwise at 0-5° C. with 8.25 mmol of boron tribromide (1M solution in dichloromethane). The reaction solution is subsequently stirred at 0° C. for 1 hour, then admixed with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (3×). The combined organic phases are dried over magnesium sulphate and evaporated. The residue is taken up in 0.5N NaOH and the mixture is extracted with ethyl acetate (3×). The combined organic phases are dried over magnesium sulphate and evaporated. The title compound is obtained as a beige solid and used without further purification for the next stage. Rt=4.91 (Gradient 1).
Workup
- extractionextracted with dichloromethane (3×)
- dry with materialThe combined organic phases are dried over magnesium sulphate
- customevaporated
- extractionthe mixture is extracted with ethyl acetate (3×)
- dry with materialThe combined organic phases are dried over magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-4ff2c4d07ee049f590a0a4a125f1d5fb
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008334B2
Reaction notes
Loading…