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

HRID 64103

Reaction equation

HRID 64103 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-10d7849704a347bea7728085636cf01c
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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