Potassium Carbonate → Methyl 3-(4-amino-1H-indazol-1-yl)benzoate

HRID 418769

反応式

HRID 418769 の反応式
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([NH2:10])[C:4]=2[CH:3]=[N:2]1.I[C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[NH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[N:2][N:1]2[C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 69258Methyl 3-iodobenzoateHCID 413085NoName_3327HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

生成物 1

HCID 57615925Methyl 3-(4-amino-1H-indazol-1-yl)benzoate収率 20.1%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

1H-Indazol-4-amine (81 mg, 0.61 mmol) and methyl 3-iodobenzoate (160 mg, 0.61 mmol) were dissolved in DMF (1 mL) in a microwave tube. Copper (I) iodide (23 mg, 0.12 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (34 mg, 0.24 mmol) and potassium carbonate (169 mg, 1.22 mmol) were added and the mixture heated by microwave (250 W) at 100° C. for 20 minutes. The mixture was filtered through a cartridge, washing with DCM (5 mL) and the filtrate was evaporated to dryness and purified by mass-directed autopreparation. The appropriate fractions were evaporated, dissolved in DCM (10 mL), washed with aqueous sodium bicarbonate, and evaporated to give the title compound (32.7 mg).

後処理

  1. filtrationThe mixture was filtered through a cartridge
  2. washwashing with DCM (5 mL)
  3. customthe filtrate was evaporated to dryness
  4. custompurified by mass-directed autopreparation
  5. customThe appropriate fractions were evaporated
  6. dissolutiondissolved in DCM (10 mL)
  7. washwashed with aqueous sodium bicarbonate
  8. customevaporated

出典と根拠

ORDレコード
ord-49835de71d8e4a398c0073584e70f4e4
出典データセット
uspto-grants-2012_01
特許番号
US08093281B2

関連ノート

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