Water → N-[3-(5-Methyl-furan-2-yl)-5-nitro-phenyl]-acetamide

HRID 64103

反応式

HRID 64103 の反応式
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.CC1(C)C(C)(C)OB([C:23]2[O:24][C:25]([CH3:28])=[CH:26][CH:27]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].O>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]>[CH3:28][C:25]1[O:24][C:23]([C:2]2[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=2)=[CH:27][CH:26]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27368814,4,5,5-Tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolaneHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

生成物 1

HCID 89500007N-[3-(5-Methyl-furan-2-yl)-5-nitro-phenyl]-acetamide収率 80%

試薬・触媒・溶媒 2

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

反応条件

温度
100 °C

実験手順

To a solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (5 g, 19.23 mmol) in 1,2-dimethoxyethane (200 ml) were added 4,4,5,5-tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane (5.9 g, 28.85 mmol), sodium carbonate (8.15 g, 76.92 mmol) and water (20 ml) and the mixture was degassed by N2 bubbling 15 min. Pd(dppf)Cl2 (3.2 g, 3.846 mmol) was added and the mixture was heated at 100° C. for 2 h. The mixture was brought to RT and quenched and extracted as in Example 1(d). The solvent was distilled off and the residue was purified by flash column chromatography (40% ethyl acetate in hexanes) to afford the product in 80% yield (4.0 g). 1H NMR (300 MHz, DMSO-d6): δ 10.45 (s, 1H), 8.4 (s, 1H), 8.2 (d, 2H), 7.1 (s, 1H), 6.2 (s, 1H), 2.4 (s, 3H), 2.15 (s, 3H), Calculated mass: 260.25; Observed mass: 259.1 [M+H]+ (rt: 1.578 min).

後処理

  1. customthe mixture was degassed by N2 bubbling 15 min
  2. customwas brought to RT
  3. customquenched
  4. extractionextracted as in Example 1(d)
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by flash column chromatography (40% ethyl acetate in hexanes)
  7. customto afford the product in 80% yield (4.0 g)
  8. custom259.1 [M+H]+ (rt: 1.578 min)

出典と根拠

ORDレコード
ord-10d7849704a347bea7728085636cf01c
出典データセット
uspto-grants-2016_09
特許番号
US09447091B2

関連ノート

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