Potassium Carbonate → 7-(1,2-dimethyl-1H-imidazol-5-yl)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79360

반응식

HRID 79360 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH2:31][CH3:32])=[N:17][N:18]4[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[CH3:49][N:50]1[CH:54]=[CH:53][N:52]=[C:51]1[CH3:55].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:49][N:50]1[C:54]([C:2]2[CH:7]=[CH:6][N:5]3[C:8]([C:11]([NH:13][C:14]4[CH:22]=[CH:21][CH:20]=[C:19]5[C:15]=4[C:16]([CH2:31][CH3:32])=[N:17][N:18]5[CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=4)=[O:12])=[CH:9][N:10]=[C:4]3[CH:3]=2)=[CH:53][N:52]=[C:51]1[CH3:55]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 156171,2-DimethylimidazoleHCID 521585Tris(furan-2-yl)phosphaneHCID 672595577-Bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

생성물 1

HCID 672601647-(1,2-dimethyl-1H-imidazol-5-yl)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide수율 15%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

To 7-bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl) imidazo[1,2-a]pyridine-3-carboxamide (prepared as in Example 127, Step A; 129 mg, 0.264 mmol) in DMF (4 mL) was added trifuran-2-ylphosphine (12.2 mg, 0.0527 mmol), 1,2-dimethyl-1H-imidazole (50.7 mg, 0.527 mmol), palladium diacetate (5.92 mg, 0.0264 mmol) and K2CO3 (72.9 mg, 0.527 mmol). The reaction mixture was purged with argon, sealed and heated to 140° C. for 3 hours. The mixture was cooled to ambient temperature, diluted with DCM (20 mL) and washed with H2O. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH/NH4OH, 10:1:0.1) to provide the final product (20 mg). MS (ES+APCI) m/z=505 (M+H).

후처리

  1. customThe reaction mixture was purged with argon
  2. customsealed
  3. temperatureThe mixture was cooled to ambient temperature
  4. additiondiluted with DCM (20 mL)
  5. washwashed with H2O
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (DCM/MeOH/NH4OH, 10:1:0.1)

출처 및 근거

ORD 기록
ord-cdaf755798a4457789dfc84e337d2c2f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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