Sodium Carbonate → 5-(1-methyl-1H-indazol-5-yl)pyridin-2(1H)-one

HRID 510303ノート

反応式

HRID 510303 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][C:15](B(O)O)=[CH:16][CH:17]=2)[CH:12]=[N:11]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(Cl)Cl.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>[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([C:2]3[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=3)=[CH:16][CH:17]=2)[CH:12]=[N:11]1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 225589101-Methyl-1H-indazole-5-boronic acidHCID 178515818HCID 178515818、化合物

生成物 1

HCID 866998355-(1-methyl-1H-indazol-5-yl)pyridin-2(1H)-one

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

The suspension of 5-bromo-2-hydroxypyridine (80 mg, 0.46 mmol), 1-methyl-1H-indazol-5-ylboronic acid (121 mg, 0.69 mmol) and 2N sodium carbonate solution (1.0 mL, 2 mmol) in DMF (2.1 mL) was degassed with N2 for 5 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium(0) (53 mg, 0.04 mmol), and the resulting mixture was heated at 80° C. overnight. The mixture was then diluted with CH2Cl2, extracted with H2O, brine, dried over Na2SO4, filtered and concentrated and purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) to give the product. LCMS-ESI+ (m/z): [M+H]+ calcd for C13H12N3O: 226.25; Found: 226.3.

後処理

  1. customwas degassed with N2 for 5 minutes
  2. extractionextracted with H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA)
  7. customto give the product

出典と根拠

ORDレコード
ord-2f313f95ed52478fb7274e2b838987f2
出典データセット
uspto-grants-2015_08
特許番号
US09096586B2

反応ノート

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