Benzyl Bromide → 1-Benzyl-6-chloro-2-isopropyl-1H-pyrrolo[3,2-c]pyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([C:9]#[C:10][CH:11]([CH3:13])[CH3:12])=[CH:4][N:3]=1.CC([O-])(C)C.[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN1C(=O)CCC1.C1COCC1.CN(C=O)C>[CH2:20]([N:8]1[C:6]2[CH:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=2[CH:9]=[C:10]1[CH:11]([CH3:13])[CH3:12])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 160 °C
Procedure
To a solution of 2-chloro-5-(3-methylbut-1-ynyl)pyridin-4-amine (Compound 12, 0.82 g, 4.2 mmol) in NMP (10 ml) was added KOtBu (2.40 g, 21 mmol). The mixture was stirred at 160° C. for 6 h and was cooled to room temperature, diluted with THF (10 ml) and DMF (15 ml). Benzyl bromide (0.50 ml, 4.2 mmol) was added. The mixture was stirred at room temperature for 16 h and was quenched with H2O, extracted with EtOAc (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a white solid.
Workup
- temperaturewas cooled to room temperature
- stirringThe mixture was stirred at room temperature for 16 h
- customwas quenched with H2O
- extractionextracted with EtOAc (×2)
- washThe combined organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)
Sources & evidence
- ORD record
- ord-5dcd1483f412422998da09c03b9c2df4
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263767B2
Reaction notes
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