Potassium Carbonate → 3-Phenyl-7-(4-phenyl-piperidin-1-ylmethyl)-imidazo[1,2-a]pyridine-8-carbonitrile
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[C:3]=1[C:17]#[N:18].C([O-])([O-])=O.[K+].[K+].C1([CH:31]([B-](F)(F)F)[N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)C=CC=CC=1.[K+]>O1CCOCC1.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]1([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([CH2:31][N:32]4[CH2:33][CH2:34][CH:35]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[CH2:36][CH2:37]4)=[C:3]([C:17]#[N:18])[C:4]3=[N:10][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 150 °C
Procedure
To a mixture of compound D6 (0.15 g, 0.593 mmol) and K2CO3 (0.35 g, 2.55 mmol) in 1,4-dioxane (4 ml) and DMF (1.5 ml) was added compound D7 (0.237 g, 0.85 mmol). The resulting mixture was degassed using a stream of nitrogen and to this was added Pd(PPh3)4 (0.098 g, 0.085 mmol). The reaction mixture was then subjected to microwave heating in a sealed tube at 150° C. for 10 min. The reaction mixture was cooled to room temperature and filtered through a pad of diatomaceous earth. The filtrate was concentrated in vacuo. The residue thus obtained was purified by preparative reverse phase HPLC to yield compound E1 (0.072 g, 31%).
Workup
- customThe resulting mixture was degassed
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered through a pad of diatomaceous earth
- concentrationThe filtrate was concentrated in vacuo
- customThe residue thus obtained
- customwas purified by preparative reverse phase HPLC
Sources & evidence
- ORD record
- ord-837bb049237b4763a4d05a1ebce919b7
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785486B2
Reaction notes
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