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Sodium Carbonate → 2,2-dimethyl-N-[2-methyl-5-[6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]phenyl]propanamide

HRID 539790
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HRID 539790 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:24])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)=[CH:10][N:4]2[N:3]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[C:32](B(O)O)=[CH:31][CH:30]=[CH:29][N:28]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(C)C.O>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18]([NH:17][C:15]1[CH:16]=[C:11]([C:9]2[N:8]=[C:5]3[N:4]([CH:10]=2)[N:3]=[C:2]([C:32]2[C:27]([C:26]([F:37])([F:36])[F:25])=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:7]=[CH:6]3)[CH:12]=[CH:13][C:14]=1[CH3:24])=[O:23]
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 44717660[2-(Trifluoromethyl)pyridin-3-yl]boronic acidHCID 86667859N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide

생성물 1

HCID 574045402,2-dimethyl-N-[2-methyl-5-[6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]phenyl]propanamide수율 33.1%

시약·촉매·용매 2

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 21889133Propan-2-ol--water (1/1)용매

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온도
80 °C

실험 절차

An 8 mL vial is charged with N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide (0.034 g, 0.0001 mol), [2-(trifluoromethyl)-3-pyridyl]boronic acid (Combi-Blocks, 0.038 g), bis(triphenylphosphine)palladium(II) dichloride (0.007 g), Na2CO3 (0.032 g), and isopropanol-water (1 mL, 3:1). The mixture is heated at 80° C. for 16 hr. The mixture is concentrated, taken up in EtOAc and CH2Cl2 (1:1), filtered, concentrated onto celite, and purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (0.015 g, 33% yield). LCMS m/z=454.6 [M+H]+, tR=2.52 min. (compound same as Example 284)

후처리

  1. concentrationThe mixture is concentrated
  2. filtrationCH2Cl2 (1:1), filtered
  3. concentrationconcentrated onto celite
  4. custompurified by silica gel chromatography (0-100% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-564cc7a68a2645cda917c8cf27a34824
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871767B2

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