Dimethylformamide → 7-(3,5-Dichloro-2-pyridinyl)-2-methyl-2H-indazole

HRID 902545Notes

Reaction equation

[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([C:5](B3OC(C)(C)C(C)(C)O3)=[CH:6][CH:7]=[CH:8]2)=[N:3]1.Cl[C:21]1[C:26]([Cl:27])=[CH:25][C:24]([Cl:28])=[CH:23][N:22]=1.CN(C=O)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O>[Cl:27][C:26]1[C:21]([C:5]2[C:4]3[C:9](=[CH:10][N:2]([CH3:1])[N:3]=3)[CH:8]=[CH:7][CH:6]=2)=[N:22][CH:23]=[C:24]([Cl:28])[CH:25]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2-methyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-indazole (0.040 g, 0.15 mmol), 2,3,5-trichloropyridine (0.274 g, 1.50 mmol), (Ph3P)4Pd(0) (0.019 g, 0.017 mmol), 2 mL of DMF, and 2 mL of a 2 M K3PO4 solution was stirred at 65° C. for. 16 h then allowed to cool. Water (10 mL) was added, and the mixture was extracted with three 5 mL portions of ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated to a brown solid. Column chromatography (0→50% EtOAc/hexanes) afforded of 7-(3,5-dichloro-pyridin-2-yl)-2-methyl-2H-indazole (7:R=Me; R′=H; Ar=3,5-dichloro-pyridin-2-yl; 0.042 g; 93%).

Workup

custom16 h
temperatureto cool
extractionthe mixture was extracted with three 5 mL portions of ethyl acetate
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated to a brown solid

Sources & evidence

ORD record: ord-fd833facfa2149db88a5d322655b2167
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365211B2

Reaction notes

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