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Sodium Iodide → Tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-8-(3-(2-oxoindolin-1-yl)propyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

HRID 1751073
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HRID 1751073 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:11](=[O:18])[N:10]([CH2:19][C:20]3[CH:21]=[C:22]([CH:30]=[CH:31][CH:32]=3)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:9]2)=[CH:4][CH:3]=1.[I-].[Na+].C(=O)(O)[O-].[K+].Cl[CH2:41][CH2:42][CH2:43][N:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:46][C:45]1=[O:53]>CC(=O)CC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]3([CH2:13][CH2:14][N:15]([CH2:41][CH2:42][CH2:43][N:44]4[C:52]5[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=5)[CH2:46][C:45]4=[O:53])[CH2:16][CH2:17]3)[C:11](=[O:18])[N:10]([CH2:19][C:20]3[CH:21]=[C:22]([CH:30]=[CH:31][CH:32]=3)[C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:9]2)=[CH:6][CH:7]=1
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6

반응물 4

HCID 5238Sodium IodideHCID 516893Potassium BicarbonateHCID 180699061-(3-Chloropropyl)indolin-2-oneHCID 66652535Tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

생성물 1

HCID 66652278Tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-8-(3-(2-oxoindolin-1-yl)propyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate수율 27%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

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온도
78 °C

실험 절차

To a solution of tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.2 g, 0.46 mmol), sodium iodide (0.021 g, 0.14 mmol) and potassium bicarbonate (0.069 g, 0.69 mmol) in 2-butanone (5 mL), was added 1-(3-chloropropyl)indolin-2-one (0.096 g, 0.46 mmol). After stirring at 78° C. for 2 hours, the reaction mixture was filtered and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-8-(3-(2-oxoindolin-1-yl)propyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.075 g, 27%).

후처리

  1. filtrationthe reaction mixture was filtered
  2. customisolated by preparatory TLC (10% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-5a89507b19fb41dca0ea578acf229ee5
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156840B2

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