Potassium Carbonate → HCID 68749923, compound

HRID 1968553Notes

Reaction equation

HRID 1968553 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]([F:13])([F:12])[F:11])=[C:6]([CH:8]=1)[NH2:7].[CH2:14]([O:16][C:17]([C:19]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[C:26](I)[N:25]=2)[N:21]([CH3:31])[CH:20]=1)=[O:18])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:14]([O:16][C:17]([C:19]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:7][C:6]3[CH:8]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[O:9][C:10]([F:11])([F:12])[F:13])[N:25]=2)[N:21]([CH3:31])[CH:20]=1)=[O:18])[CH3:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27793675-Bromo-2-(trifluoromethoxy)anilineHCID 866631235-(2-iodo-pyrimidin-4-yl)-1-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 68749923HCID 68749923, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent2×

Procedure

Palladium acetate [Pd(OAc)2] (0.12 g, 0.55 mmol), (±)-BINAP (0.34 g, 0.55 mmol) and dimethylformamide (60 mL) were charged to a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. The mixture was stirred under argon for 30 minutes and added to a mixture of 5-bromo-2-trifluoromethoxy aniline (2.0 g, 5.60 mmol), 5-(2-iodo-pyrimidin-4-yl)-1-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (1.44 g, 5.60 mmol), and potassium carbonate (7.70 g, 55.80 mmol) in dimethylformamide (90 mL). The resulting mixture was stirred at 80° C. for 3 hours under argon. After cooling to room temperature, the reaction mixture was filtered on a pad of celite. The solvent was concentrated, the crude solid was purified by flash chromatography on silica gel (eluant: hexane/ethyl acetate 70/30) to afford 1.41 g (52%) of the title compound as white solid.

Workup

  1. customflushed with argon
  2. customThe flask was evacuated
  3. stirringThe resulting mixture was stirred at 80° C. for 3 hours under argon
  4. filtrationthe reaction mixture was filtered on a pad of celite
  5. concentrationThe solvent was concentrated
  6. customthe crude solid was purified by flash chromatography on silica gel (eluant: hexane/ethyl acetate 70/30)

Sources & evidence

ORD record
ord-966de0a4b3ab4869926c306191ecc7f9
Source dataset
uspto-grants-2013_04
Patent number
US08426417B2

Reaction notes

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