Potassium Carbonate → methyl 6-amino-5-methyl-2H-indazole-7-carboxylate

HRID 245614노트

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HRID 245614 반응식
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:15])=[C:7](Br)[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4].[C:16]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:15])=[C:7]([CH3:16])[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 57990193HCID 57990193, 화합물

생성물 1

HCID 57990198methyl 6-amino-5-methyl-2H-indazole-7-carboxylate수율 43%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
180 °C

실험 절차

To a solution of 500 mg (1.85 mmol) of 6-amino-5-bromo-1H-indazole-7-carboxylic acid methyl ester, prepared as in step a in example 16, in 10 mL of dioxane under an atmosphere of argon is added 767 mg (5.55 mmol) of K2CO3, 106 mg (0.09 mmol) of tetrakis(triphenylphsophine)palladium and 232 mg (1.85 mmol) of trimethylboroxine. The reaction mixture is stirred in a microwave oven at 180° C. for 5 minutes. After filtration over Celite and concentration in vacuo, the residue is purified sequentially by flash chromatography (SiO2, hexanes/ethyl acetate 6:4) and reverse phase chromatography to afford 163 mg of product (43% over two steps) as a pale yellowish solid; LC/MS:206/207 (M+H)+.

후처리

  1. filtrationAfter filtration
  2. concentrationover Celite and concentration in vacuo
  3. customthe residue is purified sequentially by flash chromatography (SiO2, hexanes/ethyl acetate 6:4)

출처 및 근거

ORD 기록
ord-cd934c002a61467d8c2b57b6afe546f2
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658801B2

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