Nitrogen → N-(2',5'-difluoro-5-nitrobiphenyl-3-yl)acetamide

HRID 64126

반응식

HRID 64126 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.[F:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1B(O)O.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]>[F:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1

참가 물질

7

반응물 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

생성물 1

HCID 117777627N-(2',5'-difluoro-5-nitrobiphenyl-3-yl)acetamide수율 67%

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) (0.8 g, 3.07 mmol) in 1,2-dimethoxyethane (15 ml) was degassed by N2 bubbling for 5 min. 2,5-Difluorophenylboronic acid (0.58 g, 3.69 mmol, 1.2 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.5 g, 0.615 mmol, 0.2 eq.) and aqueous sodium carbonate (0.98 g, 9.23 mmol, 3.0 eq.) were added and the procedure of Example 1(d) was followed. The crude residue of the product was purified by column chromatography (60-120 silica gel, 25% ethyl acetate in hexane) to give the product in 67% yield (0.6 g). 1H NMR (300 MHz, DMSO-d6): δ 10.56 (s, 1H), 8.65 (t, 1H), 8.14 (s, 1H), 8.06 (s, 1H), 7.56-7.52 (m, 1H), 7.47-7.37 (m, 2H), 2.12 (s, 3H).

후처리

  1. customthe mixture was degassed for another 5 min
  2. customThe crude residue of the product was purified by column chromatography (60-120 silica gel, 25% ethyl acetate in hexane)
  3. customto give the product in 67% yield (0.6 g)

출처 및 근거

ORD 기록
ord-212d617d48bb4a4989bcc60b5c002bb1
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447091B2

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