1,1'-Carbonyldiimidazole → HCID 178446209, compound

HRID 2262677Notes

Reaction equation

HRID 2262677 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:5]([NH2:8])=[N:6][CH:7]=1.C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:20]([OH:21])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 59594573HCID 59594573, compound

Product 1

HCID 178446209HCID 178446209, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 100° C. solution of 5-bromo-N3-(pentan-3-yl)pyridine-2,3-diamine (2.0 g, 8.1 mmol, 1.0 equiv) in dioxane (10 mL) was added CDI portionwise until starting material was consumed as judged by TLC (50% EtOAC/Hexanes; UV). Approximately 10 equiv of carbonyldiimidazole were required. The resulting reaction mixture was cooled to room temperature, and the excess carbonyldiimidazole was quenched by the careful addition of water. The mixture was diluted with dichloromethane, and the layers were separated. The organic layer was washed with satd. aq. NaHCO3 twice, and brine once. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel MPLC provided 6-bromo-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol as a white solid (2.0 g, 74%). m/z=284.0 [M+H]+

Workup

  1. customwas consumed
  2. customThe resulting reaction mixture
  3. customthe excess carbonyldiimidazole was quenched by the careful addition of water
  4. additionThe mixture was diluted with dichloromethane
  5. customthe layers were separated
  6. washThe organic layer was washed with satd
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by silica gel MPLC

Sources & evidence

ORD record
ord-a4b652f68209458ba8544a2ab058566c
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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