Dichloromethane → 6-(3,5-dimethoxyphenyl)-3-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 1778799Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)=[N:9][N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:4]=2[CH:3]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:2]2[N:7]=[CH:6][C:5]3[C:8]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)=[N:9][N:10]([CH:11]4[CH2:16][CH2:15][CH2:14][CH2:13][O:12]4)[C:4]=3[CH:3]=2)[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.06 g, 0.2 mmol), 2-(3,5-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.060 g, 0.23 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complex with dichloromethane (1:1) (10 mg, 0.02 mmol), and potassium phosphate (80. mg, 0.38 mmol) in 1,4-dioxane (0.5 mL) and water (0.07 mL) in a reaction vial was degassed and sealed. The mixture was stirred at 90° C. for 2 h. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (80 mg). LCMS (M+H)+=420.2.

Workup

customvial was degassed
customsealed
temperatureAfter cooling it
concentrationwas concentrated under reduced pressure
customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record: ord-50aaa104f3d64fc1938ea2f6114891f2
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266892B2

Reaction notes

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