Dimethylformamide → methyl 1-(4-chlorobenzyl)-4-phenyl-1H-pyrrole-2-carboxylate

HRID 1909887Notes

Reaction equation

HRID 1909887 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH:6]=1.CN(C=O)C.[C:24]1(OB(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(OCC)(=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:5]2[CH:6]=[C:2]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:3]=[C:4]2[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 58306731methyl 4-bromo-1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 58306767methyl 1-(4-chlorobenzyl)-4-phenyl-1H-pyrrole-2-carboxylateYield 36.7%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of methyl 4-bromo-1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate (0.72 g) and DMF (21 mL) were added phenylboric acid (0.30 g), sodium carbonate (0.58 g), water (3.0 mL), and tetrakis(triphenylphosphine) palladium (0.13 g), followed by stirring at 100° C. for 24 hours. To the reaction mixture were added ethyl acetate and water, and the insoluble materials were separated by filtration through Celite. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0 to 10%) to obtain methyl 1-(4-chlorobenzyl)-4-phenyl-1H-pyrrole-2-carboxylate (0.26 g).

Workup

  1. customthe insoluble materials were separated by filtration through Celite
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=0 to 10%)

Sources & evidence

ORD record
ord-41c9e67cb03f47c0b0d706c6b2563bd7
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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