Pyrrole → HCID 58789394, compound

HRID 1175600Notes

Reaction equation

HRID 1175600 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.[NH:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cu]I>[N:18]1([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:22]=[CH:21][CH:20]=[CH:19]1

Participants

6

Reactant 3

HCID 8027PyrroleHCID 11430Potassium CarbonateHCID 687750752-(4-Bromophenyl)-N-isobutyl-2-methylpropanamide

Product 1

HCID 58789394HCID 58789394, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
195 °C

Procedure

To a solution of 2-(4-bromophenyl)-N-isobutyl-2-methylpropanamide (example 1a) (100 mg, 0.33 mmol) in DMF (5 mL) was added 1-H-pyrrole (0.66 mmol, 44 mg), K2CO3 (2.4 eq., 115 mg) and catalytic CuI (3 mg). The reaction tube was sealed, and heated in a microwave at 195° C. for 3 hours. The solution was extracted with ethyl acetate and washed with cold water. The product was purified twice by reverse phase HPLC (10 to 95% acetonitrile/water). The compound was re-dissolved in ethanol and evaporated to dryness. 1H NMR (400 MHz, DMSO-d6): δ 0.75 (d, 6H)), 1.48 (s, 6H), 1.70 (m, 1H), 2.85 (t, 2H), 6.1 (d, 2H), 7.3 (m, 5H), 7.5 (d,2H). MS: M+H=285.

Workup

  1. customThe reaction tube was sealed
  2. extractionThe solution was extracted with ethyl acetate
  3. washwashed with cold water
  4. customThe product was purified twice by reverse phase HPLC (10 to 95% acetonitrile/water)
  5. dissolutionThe compound was re-dissolved in ethanol
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-28489442bc3844b28f283e6997064a7c
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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