2-Fluoro-4-iodoaniline → 4-(2-Fluoro-4-iodophenylamino)-1-(4-methoxybenzyl)1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

HRID 79018ノート

反応式

HRID 79018 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].[F:25][C:26]1[CH:32]=[C:31]([I:33])[CH:30]=[CH:29][C:27]=1[NH2:28]>O1CCOCC1.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:28][C:27]2[CH:29]=[CH:30][C:31]([I:33])=[CH:32][C:26]=2[F:25])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 1856942-Fluoro-4-iodoanilineHCID 53665897Ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

生成物 1

HCID 673527014-(2-Fluoro-4-iodophenylamino)-1-(4-methoxybenzyl)1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester収率 56%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

4-Chloro-1-(4-methoxy-benzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (1.8 g, 5.2 mmol) and 2-fluoro-4-iodoaniline (1.5 g, 6.3 mmol) were dissolved in dioxane (20 mL) and the resultant mixture stirred at reflux for 16 hours. The reaction mixture was diluted with water (50 mL) and the aqueous layer extracted with dichloromethane (3×20 mL). The combined organic fractions were filtered through a hydrophobic frit and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0-30% ethyl acetate in cyclohexane) to yield the title compound as a white solid (1.56 g, 56%). LCMS (Method B): RT=4.78 min, [M+H]+=547.

後処理

  1. temperatureat reflux for 16 hours
  2. extractionthe aqueous layer extracted with dichloromethane (3×20 mL)
  3. filtrationThe combined organic fractions were filtered through a hydrophobic frit
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-55a10149aa2c40b5932c80cedf867b98
出典データセット
uspto-grants-2014_09
特許番号
US08841462B2

反応ノート

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