* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With thionyl chloride; In dichloromethane; at 20℃; for 2h;
Production Example 7-3: 2-Chloromethyl-6-fluoropyridine: Thionyl chloride (25 mL) was added to a dichloromethane solution (80 mL) of the compound (1.1 g) obtained in Production Example 7-2, and stirred at room temperature for 2 hours. The solvent was evaporated off under reduced pressure, ethyl acetate was added to the resulting residue, and the organic layer was washed with aqueous saturated sodium hydrogencarbonate solution. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure to obtain the entitled compound (990 mg).
2-chloro-4-(pyridin-3-yl)-5,6,7,8-tetrahydroquinoline[ No CAS ]
[ 315180-17-7 ]
2-[(6-fluoropyridin-2-yl)methoxy]-4-(pyridin-3-yl)-5,6,7,8-tetrahydroquinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
26 mg
With 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; In toluene; at 100℃; for 4h;Inert atmosphere;
Example 86 2-[(6-Fluoropyridin-2-yl)methoxy]-4-(pyridin-3-yl)-5,6,7,8-tetrahydroquinoline To 2-chloro-4-(pyridin-3-yl)-5,6,7,8-tetrahydroquinoli ne (65 mg), <strong>[315180-17-7](6-fluoropyridin-2-yl)methanol</strong> (34 mg), Pd2(dba)3·CHCl3 (17 mg), t-Bu-X-Phos (18 mg) and cesium carbonate (174 mg) was added toluene (2.6 mL), and the mixture was degassed, then stirred at 100C for 4 hours under Ar atmosphere. The mixture was filtered through Celite and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (26 mg) as colorless oil. [MS (ESI) m/z 336.2 (M+H)+]
2-chloro-4-(pyrimidin-5-yl)-5,6,7,8-tetrahydroquinoline[ No CAS ]
[ 315180-17-7 ]
2-[(6-fluoropyridin-2-yl)methoxy]-4-(pyrimidin-5-yl)-5,6,7,8-tetrahydroquinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
59 mg
With 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; In toluene; at 100℃; for 14h;Inert atmosphere;
[Step 2] Production of 2-[(6-fluoropyridin-2-yl)methoxy]-4-(pyrimidin-5-yl )-5,6,7,8-tetrahydroquinoline To 2-chloro-4-(pyrimidin-5-yl)-5,6,7,8-tetrahydroquino line (71 mg), <strong>[315180-17-7](6-fluoropyridin-2-yl)methanol</strong> (41 mg), Pd2(dba)3·CHCl3 (20 mg), t-Bu-X-Phos (33 mg) and cesium carbonate (315 mg) was added toluene (2.9 mL), and the mixture was degassed, then stirred under Ar atmosphere at 100C for 14 hours. After the reaction mixture was allowed to return to room temperature, diluted with ethyl acetate, filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (59 mg) as a pale yellow powder. [MS (ESI) m/z 337.3 (M+H)+]
2-chloro-4-(2-methylpyrimidin-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine[ No CAS ]
[ 315180-17-7 ]
2-[(6-fluoropyridin-2-yl)methoxy]-4-(2-methylpyrimidin-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
22 mg
With 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; In toluene; at 100℃; for 4h;Molecular sieve; Inert atmosphere;
Example 39 2-[(6-Fluoropyridin-2-yl)methoxy]-4-(2-methylpyrimi din-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine To 2-chloro-4-(2-methylpyrimidin-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine (100 mg), <strong>[315180-17-7](6-fluoropyridin-2-yl)methanol</strong> (62 mg), t-Bu-X-Phos (41 mg), NaO-t-Bu (78 mg), Pd2(dba)3·CHCl3 (25 mg) and MS4A was added toluene (2 mL), and the mixture was degassed, then stirred under Ar atmosphere at 100C for 4 hours. After the reaction mixture was allowed to return to room temperature, diluted with ethyl acetate, filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (22 mg) as a white powder. [MS (ESI) m/z 337.4 (M+H)+]
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