1,2-Dimethoxyethane → 6-(1-(tert-butyl)-1H-pyrazol-4-yl)-2-methylpyrazolo[1,5-a]pyridin-4-ol

HRID 2209261Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([OH:12])[C:5]2[N:6]([N:8]=[C:9]([CH3:11])[CH:10]=2)[CH:7]=1.[C:13]([N:17]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[N:18]1)([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[Cs+].[Cs+].COCCOC>O>[C:13]([N:17]1[CH:21]=[C:20]([C:2]2[CH:3]=[C:4]([OH:12])[C:5]3[N:6]([N:8]=[C:9]([CH3:11])[CH:10]=3)[CH:7]=2)[CH:19]=[N:18]1)([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture 6-chloro-2-methylpyrazolo[1,5-a]pyridin-4-ol 6.59 (17 mg), 1-(tert-butyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (19 mg), Cs2CO3 (76 mg) and PEPPSI-IPr (6 mg) was added DME and water (2:1, 3 mL) and the reaction mixture was heated to 80° C. for 2 h. The mixture was then extracted with ethyl acetate. Combined organics were washed with brine, dried, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to provide 10 mg of 6-(1-(tert-butyl)-1H-pyrazol-4-yl)-2-methylpyrazolo[1,5-a]pyridin-4-ol. LCMS [M+H]+: 271.12.

Workup

extractionThe mixture was then extracted with ethyl acetate
washCombined organics were washed with brine
customdried
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-418a3c6074fa497d9fc6894f194b9530
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

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