Potassium Carbonate → HCID 57731434, compound

HRID 2234663Notes

Reaction equation

HRID 2234663 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].[CH3:41][N:42]([CH3:50])[C:43]([CH:45]1[CH2:49][CH2:48][NH:47][CH2:46]1)=[O:44]>[Cu]I>[CH3:41][N:42]([CH3:50])[C:43]([CH:45]1[CH2:49][CH2:48][N:47]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]3=[N:6][CH:7]=2)[CH2:46]1)=[O:44]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 23090229N,N-dimethylpyrrolidine-3-carboxamideHCID 59297028HCID 59297028, compound

Product 1

HCID 57731434HCID 57731434, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

To a microwave reaction vial were added 5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (228 mg, 0.53 mmol), copper(I)-iodide (20 mg, 0.11 mmol), proline (24.4 mg, 0.21 mmol), potassium carbonate (220 mg, 1.6 mmol) and pyrrolidine-3-carboxylic acid dimethylamide (150 mg, 1.05 mmol) obtained in step 1. The mixture was flushed with nitrogen, and dimethylsulfoxide (1.5 ml) was added. The mixture was sealed and placed under microwave irradiation at 140° C. for 1 hour. The mixture was then partitioned between ethyl acetate (20 ml) and water (20 mL). The layers were separated and the aqueous layer was further extracted with ethyl acetate (10 ml). The combined organic layers were dried over Sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (0% to 100% ethyl acetate in hexanes) to give 95 mg (36%) of 1-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrrolidine-3-carboxylic acid dimethylamide. MS: m/z 495.5 (M+H+).

Workup

  1. customTo a microwave reaction
  2. customThe mixture was flushed with nitrogen, and dimethylsulfoxide (1.5 ml)
  3. additionwas added
  4. customThe mixture was sealed
  5. customplaced under microwave irradiation at 140° C. for 1 hour
  6. customThe mixture was then partitioned between ethyl acetate (20 ml) and water (20 mL)
  7. customThe layers were separated
  8. extractionthe aqueous layer was further extracted with ethyl acetate (10 ml)
  9. dry with materialThe combined organic layers were dried over Sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography (0% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-69ca80b7198243438907b0c3c9c05158
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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