Sodium Iodide → HCID 67152470, compound

HRID 552321Notes

Reaction equation

HRID 552321 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[H-].[Na+].[Br:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([N:19]2[C:23]3[N:24]=[C:25]([CH3:41])[N:26]=[C:27]([N:28]4[CH2:33][CH2:32][CH:31]([CH2:34][CH2:35]OS(C)(=O)=O)[CH2:30][CH2:29]4)[C:22]=3[C:21]([CH3:42])=[C:20]2[CH3:43])=[C:14]([CH3:44])[CH:13]=1.[Na+].[I-].OS([O-])(=O)=O.[K+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:8])[CH:5]([C:6]#[N:7])[CH2:35][CH2:34][CH:31]1[CH2:32][CH2:33][N:28]([C:27]2[C:22]3[C:21]([CH3:42])=[C:20]([CH3:43])[N:19]([C:15]4[C:16]([CH3:18])=[CH:17][C:12]([Br:11])=[CH:13][C:14]=4[CH3:44])[C:23]=3[N:24]=[C:25]([CH3:41])[N:26]=2)[CH2:29][CH2:30]1)[CH3:2]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 7764Ethyl cyanoacetate2×HCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 58281334HCID 58281334, compound

Product 1

HCID 67152470HCID 67152470, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2 atmosphere, to a solution of cyanoacetic acid ethyl ester (93 mg) in THF (3 mL) was added sodium hydride (33 mg) and the mixture was stirred for 30 minutes. Methanesulfonic acid 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethyl ester (300 mg) was added, and the mixture was heated at reflux for 3 hours. Cyanoacetic acid ethyl ester (93 mg) was added, and the reaction mixture was heated at reflux for 1 hour. And then NaI (7 mg) was added, and the mixture was heated at reflux for 2 hours. After cooling to room temperature, 5% aqueous KHSO4 solution was added into the reaction mixture and the mixture was extracted with ethyl acetate. The organic phase was dried over MgSO4 and filtered and the filtrate was concentrated under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=4/1) to obtain the title compound (57 mg) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 1 hour
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 2 hours
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe organic phase was dried over MgSO4
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=4/1)

Sources & evidence

ORD record
ord-7943b2f5f1464260b09854d4a650382b
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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