4-Bromo-2,6-difluoroaniline → HCID 66997098, compound

HRID 2360437Notes

Reaction equation

HRID 2360437 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][C:17](B3OC(C)(C)C(C)(C)O3)=[CH:18][CH:19]=2)[C:14]([CH3:30])=[N:13]1>>[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([C:2]3[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=3)=[CH:18][CH:19]=2)[C:14]([CH3:30])=[N:13]1

Participants

3

Reactant 2

HCID 6101914-Bromo-2,6-difluoroanilineHCID 595195631,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

Product 1

HCID 66997098HCID 66997098, compoundYield 39.6%

Procedure

Potassium acetate (0.344 g, 3.51 mmol) and bis(pinacolato)diboron (351 mg, 1.4 mmol) were added to a solution of 5-bromo-1,3-dimethyl-1H-indazole (240 mg, 1.06 mmol) in dioxane (10 ml) and mixture was degassed with nitrogen for 30 min. tetrakis(triphenylphosphine) palladium(0) was added and degassed for further 30 min. Reaction mixture was refluxed for 2 h. After completion of the reaction, work-up (AcOEt/H2O) followed by column afforded 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (85 mg) as a white solid. The title compound (26 mg) was prepared from 4-bromo-2,6-difluoroaniline (50 mg, 0.24 mmol) and 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (85 mg, 0.31 mmol) as a white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.93 (s, 1H), 7.66 (dd, J 1.5, 8.8, 1H), 7.55 (d, J 8.8, 1H), 7.33 (dd, J 2, 8.2, 2H), 5.22 (s, 2H), 3.94 (s, 3H), 2.49 (s, 3H).

Sources & evidence

ORD record
ord-94e58fe865f248c39731030c6c670b20
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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