Potassium Carbonate → 7-(((5-Bromo-4-chloro-2-nitrophenyl)amino)methyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one

HRID 1423846노트

반응식

HRID 1423846 반응식
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[Cl:12].[NH2:13][CH2:14][CH:15]1[CH2:30][CH2:29][CH2:28][C:17]2([O:21][C:20](=[O:22])[N:19]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:18]2)[CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:13][CH2:14][CH:15]2[CH2:30][CH2:29][CH2:28][C:17]3([O:21][C:20](=[O:22])[N:19]([CH2:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH2:18]3)[CH2:16]2)[CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 104001051-Bromo-2-chloro-5-fluoro-4-nitrobenzeneHCID 711160567-(Aminomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one

생성물 1

HCID 711160457-(((5-Bromo-4-chloro-2-nitrophenyl)amino)methyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one수율 44.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A rt suspension of 1-bromo-2-chloro-5-fluoro-4-nitrobenzene (0.600 g, 2.36 mmol) in MeCN (8 mL) was treated with 7-(aminomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (0.400 g, 1.57 mmol) and potassium carbonate (0.543 g, 3.93 mmol). The reaction was stirred for 18 h, and the solids were filtered off and washed with EtOAc. The filtrate was concentrated and purified on a 40 g silica gel column (0-100% DCM/hexanes, 20 min gradient; 100% DCM, 15 min; 40 mL/min elution; 254 nm detection) to provide the title compound (0.340 g, 44% yield) as an orange solid. MS (m/z) 488.1, 490.1 (M+H+).

후처리

  1. filtrationthe solids were filtered off
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. custompurified on a 40 g silica gel column (0-100% DCM/hexanes, 20 min gradient; 100% DCM, 15 min; 40 mL/min elution; 254 nm detection)

출처 및 근거

ORD 기록
ord-55a0e8fc57a746bf90ed4f2b1bb84814
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927585B2

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