1,2-Dimethoxyethane → HCID 59702296, compound

HRID 902551Notes

Reaction equation

HRID 902551 reaction equation
Br[C:2]1[C:10]2[C:6](=[C:7]([Cl:12])[N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1B(O)O.COCCOC.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.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>[Cl:12][C:7]1[N:8]([CH3:11])[N:9]=[C:10]2[C:6]=1[CH:5]=[CH:4][CH:3]=[C:2]2[C:17]1[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][C:18]=1[Cl:20]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 68614934HCID 68614934, compound

Product 1

HCID 59702296HCID 59702296, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
88 °C

Procedure

A mixture of 7-bromo-3-chloro-2-methyl-2H-indazole (0.079 g, 0.32 mmol), 2,4-dichlorophenyl boronic acid (0.122 g, 0.641 mmol), 2 mL of ethylene glycol dimethyl ether, 2 mL of a 2 M aqueous Na2CO3 solution, and tetrakis(triphenylphosphine)palladium(0) (0.011 g, 0.010 mmol) was stirred at 88° C. overnight, then diluted with 10 mL of ethyl acetate. The mixture was washed with two 5 mL portions of a saturated aqueous NaCl solution, dried, filtered, and concentrated to a yellow oil. Column chromatography (0→5% EtOAc/hexanes) afforded of 3-chloro-7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole (26: R=Me; Ar=2,4-dichlorophenyl; 0.063 g; 63%) as a white solid.

Workup

  1. washThe mixture was washed with two 5 mL portions of a saturated aqueous NaCl solution
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated to a yellow oil

Sources & evidence

ORD record
ord-ce9f257465fd41ba803c69a0c8a5ac13
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

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