Potassium Carbonate → HCID 86696254, compound

HRID 2175131Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.[CH3:9][N:10]1[CH:14]=[C:13](B2OC(C)(C)C(C)(C)O2)[CH:12]=[N:11]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[F:8][C:5]1[CH:4]=[CH:3][C:2]([C:13]2[CH:12]=[N:11][N:10]([CH3:9])[CH:14]=2)=[CH:7][N:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-bromo-2-fluoropyridine (1.75 g, 9.94 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.069 g, 9.94 mmol), Pd(PPh3)4 (1.149 g, 0.994 mmol) and K2CO3 (2.75 g, 19.89 mmol) in 1,4-dioxane (20 ml) was bubbled with argon for 10 min. The suspension was then stirred at 90° C. for 8 h. The mixture was filtered and the filtrate was diluted with EA, washed with water and brine. The organic phase was dried over anhydrous MgSO4, filtered and concentrated. The residue was recrystallized from MeOH to give the title compound as white solid (1.2 g, 61.3% yield). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.46 (s, 1H), 8.22 (s, 1H), 8.15 (dd, 1H), 7.93 (s, 1H), 7.18 (dd, 1H). LCMS (method B): [M+H]+=178, tR=1.80 min.

Workup

customwas bubbled with argon for 10 min
filtrationThe mixture was filtered
additionthe filtrate was diluted with EA
washwashed with water and brine
dry with materialThe organic phase was dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was recrystallized from MeOH

Sources & evidence

ORD record: ord-438e7aa2a92e4be489904e7e178f31ce
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062045B2

Reaction notes

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