Potassium Carbonate → HCID 57731521, compound

HRID 2234659Notes

Reaction equation

HRID 2234659 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:28]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>[CH3:50][N:42]([CH3:41])[C:43]([CH:45]1[CH2:49][CH2:28][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 57731521HCID 57731521, compoundYield 228.3%

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 (220 mg, 0.5 mmol), copper (I)-iodide (26 mg, 0.067 mmol), proline (0.13 mmol), potassium cabonate (280 mg, 1.5 mmol) and pyrrolidine-3-carboxylic acid dimethylamide (260 mg, 1.67 mmol). The vial was purged with nitrogen and DMSO (2.0 ml) was added. The mixture was sealed and irradiated in the microwave to 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 on silica gel (0% to 100% ethyl acetate in hexanes) to give 151 mg (˜60% with minor impurity) of 1-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-piperidine-3-carboxylic acid dimethylamide as a yellowish oil. MS: m/z 509.3 (M+H+).

Workup

  1. customTo a microwave reaction
  2. customThe vial was purged with nitrogen and DMSO (2.0 ml)
  3. additionwas added
  4. customThe mixture was sealed
  5. customirradiated in the microwave to 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 on silica gel (0% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1727e85f43354a718e17cc1a359465eb
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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