Potassium Phosphate, Dibasic → 2-Methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole

HRID 902547Notes

Reaction equation

Br[C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:14]=1B(O)O.OP([O-])([O-])=O.[K+].[K+]>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.CN(C=O)C>[CH3:11][N:8]1[CH:7]=[C:6]2[C:10]([C:2]([C:14]3[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=3[CH3:12])=[CH:3][CH:4]=[CH:5]2)=[N:9]1

Participants

Conditions

Temperature: 69 °C

Procedure

A mixture of 7-bromo-2-methyl-2H-indazole (6: R=Me; 2.01 g, 9.53 mmol), 2,4,6-trimethylphenyl boronic acid (1.70 g, 10.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.657 g, 0.569 mmol), 70 mL of DMF, and 33 mL of a 2 M aqueous K2HPO4 solution was stirred at 69° C. for 6.5 d. The mixture was partitioned between 350 mL of diethyl ether and 350 ML of water. The organic layer was washed with 350 mL of a saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated to a pale yellow oil. Column chromatography (0→33% EtOAc/hexanes) afforded of impure 2-methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole (5: R=Me, Ar=2,4,6-trimethylphenyl; 1.44 g) as a white solid that was used without further purification.

Workup

customThe mixture was partitioned between 350 mL of diethyl ether and 350 ML of water
washThe organic layer was washed with 350 mL of a saturated aqueous NaCl solution
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to a pale yellow oil

Sources & evidence

ORD record: ord-9f0828cf8e684adf858337b1d39f7eb7
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365211B2

Reaction notes

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