1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 86723765, compound

HRID 577535Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[C:9]([CH3:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:17].[CH3:18][N:19]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:20]1>C([O-])([O-])=O.[Na+].[Na+].COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][C:9]1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:11][C:2]([C:22]2[CH:21]=[N:20][N:19]([CH3:18])[CH:23]=2)=[C:3]2[C:8]=1[C:7](=[O:17])[NH:6][CH:5]=[CH:4]2

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 5-bromo-8-methyl-7-(propan-2-yloxy)isoquinolin-1(2H)-one (108h, 150 mg, 0.507 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (210 mg, 1.01 mmol) and Pd(Ph3P)4 (29 mg, 0.025 mmol) in 1M aq. Na2CO3 (1 mL) and DME (5 mL) was degassed with N2 for 3 minutes. The reaction mixture was stirred at 140° C. in the microwave for 35 minutes. The reaction mixture was dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography (EtOAc) to give 8-methyl-5-(1-methyl-1H-pyrazol-4-yl)-7-(propan-2-yloxy)isoquinolin-1(2H)-one (108i, 0.14 g, 92.9%) as a white solid.

Workup

customwas degassed with N2 for 3 minutes
dry with materialThe reaction mixture was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record: ord-df19f59c1ced4ffab03c5b33f5d55c20
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040515B2

Reaction notes

Loading…