Potassium Phosphate, Tribasic → N-(5-(6-methoxy-3-methylimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamide

HRID 539744ノート

反応式

HRID 539744 の反応式
Br[C:2]1[N:6]2[N:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([CH3:26])=[C:17]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=1.[CH3:27]B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([CH3:27])=[C:3]([C:13]3[CH:14]=[CH:15][C:16]([CH3:26])=[C:17]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=3)[N:4]=2)[N:7]=1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 68089171N-(5-(3-bromo-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamide

生成物 1

HCID 57406706N-(5-(6-methoxy-3-methylimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamide収率 6%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a mixture of N-(5-(3-bromo-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamide (0.050 g, 0.119 mmol), methylboronic acid (0.357 mmol), tripotassium phosphate (0.714 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.0238 mmol) in toluene (4 mL) and water (0.4 mL) that has been degassed with N2 (5 minutes) is added Pd(OAc)2 (0.0119 mmol). The reaction mixture is heated at 100° C. for 14 hours, then cooled and concentrated to dryness. The crude product is purified via chromatography (hexanes to EtOAc) to afford 2.4 mg (6%) of the title compound as a white solid: Rf 0.64 (EtOAc); LCMS (m/z)=353.4 [M+H]+, tR=2.15 min. (compound same as Example 121)

後処理

  1. customhas been degassed with N2 (5 minutes)
  2. temperaturecooled
  3. concentrationconcentrated to dryness
  4. customThe crude product is purified via chromatography (hexanes to EtOAc)

出典と根拠

ORDレコード
ord-34335bfcc8014e8e837bb9387c846a3d
出典データセット
uspto-grants-2014_10
特許番号
US08871767B2

反応ノート

読み込み中…