Cesium carbonate → HCID 86691856, compound

HRID 1616242Notes

Reaction equation

HRID 1616242 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][CH:13]=[CH2:14])[C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN1C(=O)CCC1.[CH2:28](I)[C:29]([CH3:32])([CH3:31])[CH3:30]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][CH:13]=[CH2:14])[C:9](=[O:11])[N:10]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 77230824HCID 77230824, compound

Product 1

HCID 86691856HCID 86691856, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

5-Chloro-3-(prop-2-en-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (71-4, 2.37 g, 11.31 mmol, 1.0 equiv) and Cs2CO3 (18.42 g, 56.6 mmol, 5.0 equiv) were added sequentially to anhydrous NMP (18.6 mL). Neopentyl iodide (2.70 mL, 20.35 mmol, 1.8 equiv) was added dropwise and the resulting mixture was heated to 100° C. for 24 h. Following this duration, the contents were cooled to RT and diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer was back-extracted with 3×50 mL EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated to give a brown semi-solid. Purification by normal-phase HPLC provided 5-chloro-1-(2,2-dimethylpropyl)-3-(prop-2-en-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (71-5) as a white solid. HRMS (M+H)+: observed=280.1207, calculated=280.1211.

Workup

  1. temperaturethe contents were cooled to RT
  2. customThe layers were separated
  3. extractionthe aqueous layer was back-extracted with 3×50 mL EtOAc
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown semi-solid
  8. customPurification by normal-phase HPLC

Sources & evidence

ORD record
ord-d0661ceee1294561bce63554bd6a585c
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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