Potassium Carbonate → HCID 59540678, compound

HRID 1677550Notes

Reaction equation

HRID 1677550 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Si](C)(C)C)[CH:15]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[I:32]Cl>C(Cl)Cl.[Al]>[I:32][C:16]1[CH:15]=[C:14]([C:11]2[N:12]=[C:13]3[C:5]([C:3](=[O:4])[C:2]([CH3:25])([CH3:24])[CH3:1])=[CH:6][NH:7][C:8]3=[N:9][CH:10]=2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24640Iodine chlorideHCID 59540956HCID 59540956, compound

Product 1

HCID 59540678HCID 59540678, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 5359268AluminumSolvent

Procedure

2,2-Dimethyl-1-[2-(3-trimethylsilanyl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (250 mg, 0.71 mmol) was suspended in 7 ml of methylene chloride and potassium carbonate (393 mg, 2.8 mmol) was added. The flask was wrapped in aluminum foil and iodine monochloride (2.5 ml of a 1M solution in methylene chloride) was added dropwise. The mixture was stirred in the dark at room temperature for one hour. The reaction was quenched with 10% aqueous sodium thiosulfate, extracted into methylene chloride, and washed with water two times. The organic layer was dried with sodium sulfate, concentrated, triturated with ethyl ether, filtered and dried in a vacuum oven to give 232 mg (81%) of 1-[2-(3-iodo-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2,-dimethyl-propan-1-one as a yellow solid. (M+H)+=406.

Workup

  1. additionwas added dropwise
  2. customThe reaction was quenched with 10% aqueous sodium thiosulfate
  3. extractionextracted into methylene chloride
  4. washwashed with water two times
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated
  7. customtriturated with ethyl ether
  8. filtrationfiltered
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-6b4dd41255914e118475a072b57f3fd9
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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