Potassium Carbonate → HCID 117987982, compound

HRID 2206111Notes

Reaction equation

HRID 2206111 reaction equation
C[O:2][C:3]1[C:8]2[NH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:7]=2[C:6]([C:19]#[N:20])=[CH:5][N:4]=1.Br[C:22]1[CH:23]=[C:24]([C:27]([NH2:29])=[O:28])[S:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>[Cu]I.O>[C:19]([C:6]1[C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:10][N:9]([C:22]3[CH:23]=[C:24]([C:27]([NH2:29])=[O:28])[S:25][CH:26]=3)[C:8]=2[C:3](=[O:2])[NH:4][CH:5]=1)#[N:20]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 128360674-Bromothiophene-2-carboxamideHCID 117988564HCID 117988564, compound

Product 1

HCID 117987982HCID 117987982, compoundYield 3.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 7-methoxy-3-(2-methylphenyl)-1H-pyrrolo[2,3-c]pyridine-4-carbonitrile (50 mg), 4-bromothiophene-2-carboxamide (47 mg), copper(I) iodide (3.6 mg), potassium carbonate (31.5 mg) and N-methylpyrrolidone (2 mL) was stirred under microwave irradiation at 200° C. for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane, methanol/ethyl acetate). The obtained fraction was purified by HPLC (C18, mobile phase: water/acetonitrile (containing 5 mM ammonium carbonate)), to the obtained fraction was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (2.5 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane, methanol/ethyl acetate)
  6. customThe obtained fraction was purified by HPLC (C18, mobile phase: water/acetonitrile (containing 5 mM ammonium carbonate)), to the obtained fraction
  7. additionwas added saturated aqueous sodium hydrogencarbonate solution
  8. extractionthe mixture was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c9855d6442064a20a38496c2fde4a400
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

Loading…