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

HRID 245614ノート

反応式

HRID 245614 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 57990193HCID 57990193、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
180 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-cd934c002a61467d8c2b57b6afe546f2
出典データセット
uspto-grants-2014_02
特許番号
US08658801B2

反応ノート

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