Ethanol → 2-(4-(Furan-3-yl)phenyl)-N-isobutyl-2-methylpropanamide

HRID 1175564Notes

Reaction equation

HRID 1175564 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])=[CH:4][CH:3]=1.CCO.C([O-])([O-])=O.[K+].[K+].[O:27]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28]1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:27]1[CH:31]=[CH:30][C:29]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])=[CH:4][CH:3]=2)=[CH:28]1

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2734358Furan-3-boronic acidHCID 687750752-(4-Bromophenyl)-N-isobutyl-2-methylpropanamide

Product 1

HCID 587893422-(4-(Furan-3-yl)phenyl)-N-isobutyl-2-methylpropanamideYield 41%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-Bromophenyl)-N-isobutyl-2-methylpropanamide (Example 1a) (850 mg, 2,85 mmol) was dissolved in 30 ml of toluene, 6 ml of EtOH and 4.5 ml of water followed by 1.38 g (10 mmol) of K2CO3 and 560 mg (5 mmol) of 3-furanboronic acid. The suspension was degassed using argon stream and sonication (30 min). Then 1.16 g (1 mmol) of tetrakis(triphenylphosphine)palladium was added under argon and the mixture was stirred at 80° C. overnight. The solution was dried down on vacuum, diluted with EtOAc and extracted with water. The organic phase was dried over MgSO4 and evaporated on vacuum providing a crude product that was further purified using RP HPLC yielding 300 mg (41%) of the title compound as a white solid. 1H NMR (400 MHz, dDMSO): δ 0.74-0.75 (d 6H), 1.45 (s, 6H), 1.67-1.70 (m,1H), 2.83-2.86 (dd, 2H), 6.94-6.95 (dd, 1H), 7.30-7.32 (m, 3H), 7.54-7.57 (m, 2H), 7.72-7.73 (t, 1H), 8.15-8.16 (t, 1H). MS (M+H, 286).

Workup

  1. customThe suspension was degassed
  2. customargon stream and sonication (30 min)
  3. customThe solution was dried down on vacuum
  4. additiondiluted with EtOAc
  5. extractionextracted with water
  6. dry with materialThe organic phase was dried over MgSO4
  7. customevaporated on vacuum
  8. customproviding a crude product that
  9. customwas further purified

Sources & evidence

ORD record
ord-19fafe00ce824b6bbbbd585a2cb997d0
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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