4-bromo-N-tert-butylbenzamide → HCID 11609336, compound
Reaction equation
C([Li])CCC.Br[C:7]1[CH:19]=[CH:18][C:10]([C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][CH:8]=1.[CH:20]1[N:21]=[CH:22][N:23]2[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[C:24]=12>O1CCCC1>[C:14]([NH:13][C:11](=[O:12])[C:10]1[CH:18]=[CH:19][C:7]([C:25]2([OH:29])[CH2:26][CH2:27][CH2:28][N:23]3[CH:22]=[N:21][CH:20]=[C:24]23)=[CH:8][CH:9]=1)([CH3:17])([CH3:16])[CH3:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
11.6 ml of n-butyllithium (1.6M in hexane) are added dropwise to a solution of 4.250 mmol of 4-bromo-N-tert-butylbenzamide in 200 ml of tetrahydrofuran at −78° C. After 90 minutes, a solution of 6.00 mmol of 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one [51907-18-7] in 4 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred at −78° C. for 1 hour and at room temperature for 2 hours and then quenched with saturated aqueous ammonium chloride solution. The organic phase is separated off and the aqueous phase is extracted with ethyl acetate (2×). The combined organic phases are dried with sodium sulphate and evaporated. The title compound is obtained as a yellow solid from the residue by flash chromatography (SiO2 60F). Rf=0.16 (dichlormethane:methanol=95:5), Rt=4.96.
Workup
- customquenched with saturated aqueous ammonium chloride solution
- customThe organic phase is separated off
- extractionthe aqueous phase is extracted with ethyl acetate (2×)
- dry with materialThe combined organic phases are dried with sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-c443d44d7ceb415eb11f581d7bf1e7ea
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680079B2
Reaction notes
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