Water → 5-[N-(cyclopentylmethyl)-N-ethylamino]-1,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile
Reaction equation
Br[C:2]1[C:6]2=[N:7][C:8]([N:13]([CH2:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:14][CH3:15])=[C:9]([C:11]#[N:12])[CH:10]=[C:5]2[N:4]([CH3:22])[CH:3]=1.[CH3:23][Mg]Br.O>C1COCC1>[CH:17]1([CH2:16][N:13]([C:8]2[N:7]=[C:6]3[C:2]([CH3:23])=[CH:3][N:4]([CH3:22])[C:5]3=[CH:10][C:9]=2[C:11]#[N:12])[CH2:14][CH3:15])[CH2:21][CH2:20][CH2:19][CH2:18]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A mixture of 3-bromo-5-[N-(cyclopentylmethyl)-N-ethylamino]-1-methyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (1.05 g, 2.91 mmol) and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane complex (PdCl2(dppf)-CH2Cl2, 0.24 g, 0.29 mmol) in THF (20 mL) is treated with methylmagnesium bromide (0.93 M in THF, 7.8 mL) at 0° C. The reaction mixture is stirred at 75° C. for 22 hours. After cooling to room temperature, H2O is added, and the reaction mixture is extracted with EtOAc. The organic layer is washed with sat. NaHCO3 and brine, dried over sodium sulfate and concentrated. The residue is purified by silica-gel column chromatography to give 5-[N-(cyclopentylmethyl)-N-ethylamino]-1,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile as a colorless oil.
Workup
- temperatureAfter cooling to room temperature
- extractionthe reaction mixture is extracted with EtOAc
- washThe organic layer is washed with sat. NaHCO3 and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue is purified by silica-gel column chromatography
Sources & evidence
- ORD record
- ord-449f13a8b1fe40aabba2811e5bc47ea3
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410275B2
Reaction notes
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