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With hydrogenchloride; hydrogen;palladium dihydroxide; In methanol; water; under 2585.81 Torr; for 36h;
4-Methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine 5. A suspension of (4-methoxy-1 H- pyrrolo[2,3-b]pyridin-2-yl)methanol 4 (0.90 g, 5.05 mmol) and Pd(OH)2 (100 mg) in methanol containing 4N aq. HCI solution (10 mL) was hydrogenated under hydrogen pressure (50 psi) for 36 h. The acidic mixture was quenched with 1 N NaOH solution. Filtration through celite, concentration and purification on silica gel column using 5% methanol in CH2CI2 to gave 5 as pale yellow syrup. Yield: 0.68 g, 83%; ESI MS: m/z 163.01 (M+1).
83%
[00570] 4-Methoxy-2-methyMH-pyrrolo[2,3-b]pyiotadine 5. A suspension of (4- methoxy-1H-pyrrolo[2,3-ib]pyridin-2-yl)methanol 4 (0.90 g, 5.05 mmol) and Pd(OH)2 (100 mg) in methanol containing 4N aq. HCI solution (10 mL) was hydrogenated under hydrogen pressure (50 psi) for 36 h. The acidic mixture was quenched with 1 N NaOH solution. Filtration through celite, concentration and purification on silica gel column using 5% methanol in CH2CI2 to gave 5 as pale yellow syrup. Yield: 0.68 g, 83%; ESI MS: m/z 163.01 (M+1).
83%
A suspension of (4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol 4 (0.90 g, 5.05 mmol) and Pd(OH)2 (100 mg) in methanol containing 4N aq. HCl solution (10 mL) was hydrogenated under hydrogen pressure (50 psi) for 36 h. The acidic mixture was quenched with 1N NaOH solution. Filtration through celite, concentration and purification on silica gel column using 5% methanol in CH2Cl2 to gave 5 as pale yellow syrup. Yield: 0.68 g, 83%; ESI MS: m/z 163.01 (M+1).
[00571] 1-Benzyl-4-nmethoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine 6. To a suspension of sodium hydride (0.292 g, 9.24 mmol) in dry N,N-dimethyl acetamide (10 mL) was added drop-wise under N2, a solution of <strong>[307951-52-6]4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine</strong> 5 (0.60 g, 3.70 mmol) in the same solvent (5 mL). The mixture was stirred at room temperature for 45 min. After this time, the solution was cooled in an ice bath, and benzyl bromide (1.25 g, 7.30 mmol) was slowly added. The solution was allowed to warm at room temperature and stirred for 12 h. Then, it was poured into ice water (30 mL) and stirred for 30 min, and the precipitated solid was extracted with ethylacetate (3x20 mL). The organic layer was washed with water and brine. Concentration and purification on silica gel column using 20% ethylacetate in hexanes gave pure title compound 6 as a white solid. Yield: 0.70 g, 68%; mp 129-131 0C; ESI MS: m/z 253.0 (M+1).
68%
To a suspension of sodium hydride (0.292 g, 9.24 mmol) in dry N,N-dimethyl acetamide (10 mL) was added drop-wise under N2, a solution of <strong>[307951-52-6]4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine</strong> 5 (0.60 g, 3.70 mmol) in the same solvent (5 mL). The mixture was stirred at room temperature for 45 min. After this time, the solution was cooled in an ice bath, and benzyl bromide (1.25 g, 7.30 mmol) was slowly added. The solution was allowed to warm at room temperature and stirred for 12 h. Then, it was poured into ice water (30 mL) and stirred for 30 min, and the precipitated solid was extracted with ethylacetate (3×20 mL). The organic layer was washed with water and brine. Concentration and purification on silica gel column using 20% ethylacetate in hexanes gave pure title compound 6 as a white solid. Yield: 0.70 g, 68%; mp 129-131 C.; ESI MS: m/z 253.0 (M+1).
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