4-Bromo-2,6-difluoroaniline → HCID 66997098、化合物

HRID 2360437ノート

反応式

HRID 2360437 の反応式
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

参加物

3

反応物 2

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

生成物 1

HCID 66997098HCID 66997098、化合物収率 39.6%

実験手順

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).

出典と根拠

ORDレコード
ord-94e58fe865f248c39731030c6c670b20
出典データセット
uspto-grants-2014_04
特許番号
US08686048B2

反応ノート

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