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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 1h;
Step B: Preparation of 3-Bromoimidazo[l,2-alpha]pyridine-8-carboxylic Acid.Imidazo[l,2-alpha]pyridine-8-carboxylic acid (100 mg, 617 mumol), l-bromopyrrolidine-2,5- dione (110 mg, 617 mumol) and N,N-dimethylformamide (1.5 mL) were stirred at room temperature for 1 h. The resulting precipitate was filtered off and washed with acetonitrile and hexane to afford the title compound as a solid (68 mg).
With triethylamine; HATU In tetrahydrofuran at 100℃; for 0.333333h; microwave irradiation;
1.1.C
Step C: Preparation of (3-Bromoimidazo[l,2-α]pyridin-8-yl)(4-(2,4- difluorophenethyl)piperazin-l-yl)methanone (Compound 9). l-(2,4-Difiuorophenethyl)piperazine hydrochloride (84 mg, 0.28 mmol) was added to a solution of 3-bromoimidazo[l,2-α]pyridine-8-carboxylic acid (68 mg, 0.28 mmol), 2-(3H- [1 ,2,3]triazolo[4,5-6]pyridin-3-yl)-l , 1 ,3,3-tetramethylisouronium hexafluorophosphate (ηATU) (138 mg, 364 μmol) and triethylamine (117 μL, 840 μmol) in TηF (2.7 mL). The reaction mixture was heated at 100 0C under microwave irradiation for 20 min. The solvent was removed under reduced pressure and the residue was purified by preparative ηPLC to afford the TFA salt of the title compound as a solid (162 mg).
3-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl)-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)imidazo[1,2-a]pyridine-8-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 2 steps
1: 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dimethyl sulfoxide / 20 °C
2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 80 °C / Inert atmosphere
(3-bromoimidazo[1,2-a]pyridin-8-yl)(pyrrolidin-1-yl)methanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Stage #1: 3-bromoimidazo[1,2-a]pyridine-8-carboxylic acid With N-ethyl-N,N-diisopropylamine; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: pyrrolidine In N,N-dimethyl-formamide at 20℃; for 0.666667h;
11.19.1 Step 1. (3-Bromoimidazo[1,2-a]pyridin-8-yl)(pyrrolidin-1-yl)methanone F17-1
A solution of 3-bromo-imidazo[1,2-a] pyridine-8-carboxylic acid (362 mg, 1.5 mmol), TBTU (530 mg, 1.650 mmol) and DIPEA (0.288 mL, 1.650 mmol) in DMF (5 mL) was stirred at rt for 10 min. Pyrrolidine (0.136 mL, 1.650 mmol) was then added and stirring was continued for 40 min at rt. The reaction mixture was partitioned between EtOAc (50 mL) and 5% aq. NaHCO3(10 mL). The organic phase was washed with 5% aq. NaHCO3solution (2 x 10 mL) and brine (10 mL), dried over Na2SO4, filtered, and concentrated to dryness in vacuo to afford F17-1 (440 mg, 1.301 mmol, 87% yield) as a brown oil which was used in the next step without purification. Analytical method 10; tR= 0.69 min; [M+H]+= 294.0.
3-bromo-8-(pyrrolidin-1-ylmethyl)imidazolo[1,2-a]pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 2 steps
1.1: O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C
1.2: 0.67 h / 20 °C
2.1: dimethylsulfide borane complex / tetrahydrofuran / 5.5 h / 60 °C
2.2: 21.5 h / 15 - 60 °C
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