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With triethylamine;dmap; In dichloromethane; at 20℃;
A round-bottom flask was charged with Int-15 (6.6 g, 45 mmol), (BoC)2O (10.7 g, 50 mmol), 4-dimethylaminopyridine (55 mg, 0.45 mmol), triethylamine (13 g, 130 mmol), and DCM (50 mL). The mixture was stirred at room temperature overnight, concentrated to dryness, and purified by flash column chromatography to afford product Int-16 (9.8 g, 89%).
82%
With dmap; In acetonitrile; at 20℃; for 6.5h;
To a suspension of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (304 mg, 2.08 mmol; commerciallyavailable from, for example, Enamine) and di-tett-butyl dicarbonate (0.580 mL, 2.50 mmol) inacetonitrile (5 mL) was added DMAP (28 mg, 0.23 mmol) and the reaction mixture stirred at rt under nitrogen for 6.5 h before being left to stand overnight. The reaction mixture was concentrated in vacuo to give a brown solid which was dissolved in dichloromethane (3 mL) and loaded onto a 25 g SNAP silica cartridge and purified by flash chromatography eluting with a gradient of 3O-5O% ethylacetate in cyclohexane. The required fractions were combined and concentrated in vacuo before the residue was dissolved in dichloromethane (6 mL), transferred to a tarred vial, concentrated under a stream of nitrogen and dried in vacuo to give a white solid; ter1butyl 3-formyl-1H-pyrrolo[2,3- b]pyridine-1-carboxylate (420.7 mg, 1.71 mmol, 82 % yield).LCMS (2 mm high pH) Rt = 0.97 mi m/z= 247 for [MH]
With dmap; triethylamine; In acetonitrile; at 0 - 20℃; for 18.0h;
To an acetonitrile solution (0.2 M) of lH-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1 eq.) was added triethylamine (1.05 eq.), DMAP (0.3 eq.) and di-tert-butyl carbonate (1.2 eq.) at 0 0C. The resulting mixture was allowed to warm slowly to RT over 18 h. The resulting mixture was then diluted with water and extracted with EtOAc. The combined organic extracts were washed further with sat. aq. NH4Cl, sat. aq. NaHCO3 and brine, dried over Na2SO4 and filtered.
0.779 g
With dmap; In acetonitrile; at 20℃;
General procedure: To a solution of an appropriate indole, azaindole or alternative heterocycles (1.0 eq) and di-ferf-butyl dicarbonate (1eq. to 2 eq., more in particular 1.2 eq) in acetonitrile was added DMAP (0.1 to 0.5 eq. more in particular 0.1 eq). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated sodium bicarbonate solution. The phases were separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with a saturated ammonium chloride solution, water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The BOC-protected compound was used in the next step without further purification.
(E)-3-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)thiochroman-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
48%
With hydrogenchloride; In methanol; water; at 60 - 80℃; for 6h;
General procedure: To a solution of (7) 1-(1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (0.300g, 2.053mmol) in 32% aqueous HCl/methanol (1.5:1 v/v) (4.5ml/3 ml) was added a selected bicyclic scaffold (tetralone, indanone, 3-coumaranone, 4-chromanone and thiochroman-4-one) (2.053mmol) and the reaction was refluxed for at least 6h at 60-80C. The progress of the reaction was monitored by silica gel TLC with ethyl acetate as mobile phase. When the reaction reached completion, the target products were isolated by precipitation with ice-cold water, after which they were purified by recrystallisation with ethanol.
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