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

HRID 418769

반응식

HRID 418769 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-49835de71d8e4a398c0073584e70f4e4
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093281B2

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