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

HRID 539744노트

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HRID 539744 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-34335bfcc8014e8e837bb9387c846a3d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871767B2

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