Potassium Carbonate → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79382ノート

反応式

HRID 79382 の反応式
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.[N:33]1[CH:34]=[CH:35][N:36]2[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][C:37]=12.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH2:31]([C:16]1[C:15]2[C:19](=[CH:20][CH:21]=[CH:22][C:14]=2[NH:13][C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([C:35]4[N:36]5[CH2:41][CH2:40][NH:39][CH2:38][C:37]5=[N:33][CH:34]=4)=[CH:3][C:4]3=[N:10][CH:9]=2)=[O:12])[N:18]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=2)[N:17]=1)[CH3:32]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 21955306tert-Butyl 5,6-dihydroimidazo(1,2-a)pyrazine-7(8H)-carboxylateHCID 672595577-Bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

生成物 1

HCID 53262090N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide収率 26.3%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

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; 50 mg, 0.10 mmol) in DMF (4 mL) was added tert-butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate (68 mg, 0.31 mmol), Pd(PPh3)4 (12 mg, 0.01 mmol), palladium diacetate (2.3 mg, 0.010 mmol) and K2CO3 (42 mg, 0.31 mmol). The reaction mixture was purged with argon and the reaction vial was sealed and the mixture was heated to 140° C. for 3 hours. The mixture was cooled to ambient temperature and diluted with DCM (20 mL). The solution was washed with H2O, 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 (14 mg). MS (ES+APCI) m/z=532 (M+H).

後処理

  1. customThe reaction mixture was purged with argon
  2. customthe reaction vial was sealed
  3. temperatureThe mixture was cooled to ambient temperature
  4. additiondiluted with DCM (20 mL)
  5. washThe solution was washed with H2O
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1)

出典と根拠

ORDレコード
ord-50c00976280348d0b5e801d60b2b650b
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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