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

HRID 902547

反応式

HRID 902547 の反応式
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

参加物

6

反応物 3

HCID 24450Potassium Phosphate, DibasicHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 210945807-bromo-2-methyl-2H-indazole

生成物 1

HCID 210945602-Methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole収率 60.4%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
69 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-9f0828cf8e684adf858337b1d39f7eb7
出典データセット
uspto-grants-2008_04
特許番号
US07365211B2

関連ノート

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