Ethyl Acetate → 6-chloro-3-(methoxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 571383Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](I)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[CH3:31][O:32][CH2:33][B-](F)(F)F.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Pd+2]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH2:31][O:32][CH3:33])=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Under Argon, the solution of 6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine (52 mg, 0.100 mmol), potassium methoxymethyltrifluoroborate (16.66 mg, 0.110 mmol), palladium(II) acetate (0.671 mg, 2.99 μmol), (2-DICYCLOHEXYLPHOSPHINO-2′,6′-DIISOPROPYL-1,1′-BIPHENYL)[2-(2-AMINOETHYL)PHENYL)]PALLADIUM(II) (4.36 mg, 5.98 μmol and cesium carbonate (0.024 ml, 0.299 mmol) in 1,4-Dioxane (0.9 ml) and Water (0.1 ml) was allowed to stir at 100° C. for 24 h. LC-MS showed the desired product's mass. EtOAc was added into the mixture and the organic layer was washed by water and brine. After drying over Na2SO4 the organic layer was evaporated under reduced pressure yielding 6-chloro-3-(methoxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine, 52a. The intermediate was taken to the next reaction without further purification. MS ESI Calc'd for C27H22ClN3O [M+H]+ 440, found 440.

Workup

washthe organic layer was washed by water and brine
dry with materialAfter drying over Na2SO4 the organic layer
customwas evaporated under reduced pressure

Sources & evidence

ORD record: ord-0ecdedde8bb748fdbddddd7a0aae9312
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023865B2

Reaction notes

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