1,2-Dimethoxyethane → N,N-diallyl-4-(3-(5-chloro-6-methoxypyridin-3-yl)phenylsulfonamido)pyridine-3-sulfonamide

HRID 2283343노트

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HRID 2283343 반응식
[CH2:1]([N:4]([CH2:25][CH:26]=[CH2:27])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3].[Cl:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][C:34]=1[O:35][CH3:36].C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH2:1]([N:4]([CH2:25][CH:26]=[CH2:27])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:31]2[CH:32]=[N:33][C:34]([O:35][CH3:36])=[C:29]([Cl:28])[CH:30]=2)[CH:19]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3]

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 24901777(5-Chloro-6-methoxypyridin-3-yl)boronic acidHCID 57750923N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamide

생성물 1

HCID 57750978N,N-diallyl-4-(3-(5-chloro-6-methoxypyridin-3-yl)phenylsulfonamido)pyridine-3-sulfonamide수율 58%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매

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온도
100 °C

실험 절차

A mixture of N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamide (0.29 g, 0.62 mmol), 5-chloro-6-methoxypyridin-3-ylboronic acid (0.15 g, 0.81 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.026 g, 0.030 mmol), cesium carbonate (0.30 g, 0.93 mmol), 1,2-dimethoxyethane (4.5 mL) and water (0.5 mL) under an atmosphere of argon was heated at 100° C. for 15 min in a microwave reactor. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (98:2) as the eluent, gave the title compound in 58% yield.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated
  4. customPurification by column chromatography

출처 및 근거

ORD 기록
ord-fdc6b04dd0de4f7baf7ddd51aadebe30
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145380B2

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