Nitrogen → N-(3-(benzofuran-2-yl)-5-nitrophenyl)acetamide

HRID 64129

반응식

HRID 64129 반응식
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.N#N.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

참가 물질

7

반응물 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 10658908N-(3-bromo-5-nitrophenyl)acetamideHCID 113685332-(1-Benzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 89500178N-(3-(benzofuran-2-yl)-5-nitrophenyl)acetamide

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (2 g, 7.7 mmol) in 1,2-dimethoxyethane (25 ml) was degassed by N2 bubbling for 5 min. 2-(Benzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.45 g, 10 mmol, 1.3 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.63 g, 0.77 mmol, 0.1 eq.) and aqueous sodium carbonate (2.45 g, 23.1 mmol, 3.0 eq.) were added and the procedure of Example 1(d) was followed. The crude residue of the product was directly used for the next step.

후처리

  1. customthe mixture was degassed for another 5 min

출처 및 근거

ORD 기록
ord-1e27b309856a4d778203c36fa0fb4ba4
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447091B2

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