Water → HCID 178461595、化合物

HRID 522814ノート

反応式

HRID 522814 の反応式
Br[C:2]1[NH:3][C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@H:12]1[CH3:17])[N:7]=[C:6]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][C@H:19]1[CH3:24])[N:5]=2.O.[NH:26]1[CH:30]=[CH:29][N:28]=[C:27]1[C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.[F-].[Cs+]>C(#N)C.C(Cl)Cl.C(O)(C)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>[NH:26]1[CH:30]=[CH:29][N:28]=[C:27]1[C:31]1[CH:36]=[CH:35][C:34]([C:2]2[NH:3][C:4]3[C:9]([N:10]=2)=[C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@H:12]2[CH3:17])[N:7]=[C:6]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][C@H:19]2[CH3:24])[N:5]=3)=[CH:33][CH:32]=1

参加物

9

反応物 4

HCID 962WaterHCID 25953Cesium fluorideHCID 66575043(4-(1H-Imidazol-2-yl)phenyl)boronic acidHCID 178461594HCID 178461594、化合物

生成物 1

HCID 178461595HCID 178461595、化合物収率 50.4%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 3776Isopropanol溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

8-Bromo-2,6-bis-((R)-3-methyl-morpholin-4-yl)-9H-purine (99 mg, 250 μmol) was dissolved in 2 mL of acetonitrile and 0.2 mL of water under argon. 4-(1H-imidazol-2-yl)phenyl boronic acid (58.7 mg, 313 μmol), CsF (57 mg, 375 μmol), and Pd(PPh3)4 (28.9 mg, 25 μmol) were added. The suspension was stirred at 50° C. for 10 minutes in a closed microwave vial. Then it was irradiated for 40 minutes in a microwave apparatus at 150° C. The vial was cooled and uncapped, and the reaction mixture was diluted with 50 mL of CH2Cl2 and 10 mL of isopropanol. The organic solvents were washed with brine and aqueous NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (40 g SiO2, CH2Cl2/EtOH/aqueous NH3 in a gradient from 100/0/0.1 to 90/10/0.1) to give the product as a solid (58 mg, 48%).

後処理

  1. customThen it was irradiated for 40 minutes in a microwave apparatus at 150° C
  2. temperatureThe vial was cooled
  3. washThe organic solvents were washed with brine and aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (40 g SiO2, CH2Cl2/EtOH/aqueous NH3 in a gradient from 100/0/0.1 to 90/10/0.1)

出典と根拠

ORDレコード
ord-6a5c567c6cf84e85a83f7265ee75d0bc
出典データセット
uspto-grants-2016_05
特許番号
US09334271B2

反応ノート

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