Potassium Carbonate → tert-butyl N-(4-chloro-5-methyl-2-nitrophenyl)carbamate

HRID 498170노트

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HRID 498170 반응식
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12](Cl)[C:11]([Cl:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])([CH3:4])([CH3:3])[CH3:2].[C:20](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12]([CH3:20])[C:11]([Cl:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 69489445tert-butyl N-(4,5-dichloro-2-nitrophenyl)carbamate

생성물 1

HCID 69489578tert-butyl N-(4-chloro-5-methyl-2-nitrophenyl)carbamate수율 48%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

To a suspension of (4,5-dichloro-2-nitro-phenyl)-carbamic acid tert.-butyl ester (Example A20) (10.0 g, 32.6 mmol), tetrakis(triphenylphosphine)palladium (3.76 g, 3.26 mmol) and potassium carbonate (13.5 g, 97.7 mmol) in dioxane/water (9:1; 100 ml) was added at RT trimethylboroxine (4.53 ml, 32.6 mmol). The reaction mixture was stirred under reflux conditions for 15 h, filtered, evaporated and purified by column chromatography on silica gel (hexane/ethyl acetate 19:1) to yield a light yellow solid (4.45 g, 48%).

후처리

  1. filtrationfiltered
  2. customevaporated
  3. custompurified by column chromatography on silica gel (hexane/ethyl acetate 19:1)

출처 및 근거

ORD 기록
ord-f49d5c4f06e14d1ba1719cbece00105c
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949542B2

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