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

HRID 79018노트

반응식

HRID 79018 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-55a10149aa2c40b5932c80cedf867b98
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841462B2

반응 노트

불러오는 중…