1,2-Dimethoxyethane → 7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole-3-carboxylic acid methyl ester

HRID 902559Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:15])[N:7]=[C:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2Br)=[O:4].[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1B(O)O.COCCOC.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:15])[N:7]=[C:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[C:20]1[CH:19]=[CH:18][C:17]([Cl:16])=[CH:22][C:21]=1[Cl:23])=[O:4]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 35a (0.750 g, 2.79 mmol), 2,4-dichlorophenyl boronic acid (1.06 g, 5.57 mmol), 10 mL of ethylene glycol dimethyl ether, tetrakis(triphenylphosphine) palladium(0) (0.097 g, 0.084 mmol), and 10 mL of a 2 M aqueous Na2CO3 solution was stirred at 85° C. overnight, then allowed to cool. Ethyl acetate (50 mL) was added, and the mixture was washed with 30 mL of a saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated to a yellow oil. Column chromatography (0→10% EtOAc/hexanes) afforded of 7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole-3-carboxylic acid methyl ester (35b: 0.582 g; 62%; m.p. 128-131) as a white solid:

Workup

temperatureto cool
washthe mixture was washed with 30 mL of a saturated aqueous NaCl solution
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to a yellow oil

Sources & evidence

ORD record: ord-7306293931c64a89b980a836c8dacd34
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365211B2

Reaction notes

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