Ammonium Chloride → HCID 69434808, compound

HRID 1890633Notes

Reaction equation

HRID 1890633 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:17]([C:19]1[N:29]([CH2:30][C:31]2[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=2)[CH:34]=[O:35])[C:22]2=[N:23][C:24]([CH3:28])=[CH:25][C:26]([CH3:27])=[C:21]2[N:20]=1)[CH3:18].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Si:8]([O:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([CH:34]([C:33]2[CH:36]=[CH:37][CH:38]=[C:31]([CH2:30][N:29]3[C:22]4=[N:23][C:24]([CH3:28])=[CH:25][C:26]([CH3:27])=[C:21]4[N:20]=[C:19]3[CH2:17][CH3:18])[CH:32]=2)[OH:35])=[CH:3][CH:4]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 108595834-Bromobenzyloxy-tert-butyldimethylsilaneHCID 23156187HCID 23156187, compound

Product 1

HCID 69434808HCID 69434808, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

4-Bromobenzyloxy-tert-butyldimethylsilane (1.23 g, 4.08 mmol) obtained in Step 1 was dissolved in THF (30 mL) and the flask was filled with argon. The reaction mixture was cooled to −78° C., and a 1.57 mol/L n-butyl lithium-hexane solution (2.60 mL, 4.09 mmol) was added thereto, followed by stirring at same temperature for 5 minutes. A solution of 3-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)benzaldehyde (0.800 g, 2.72 mmol) obtained in Step 2 in THF (5 mL) was dropped into the mixture for 15 minutes, followed by stirring at −78° C. for 1 hour. The reaction mixture was added with a saturated aqueous ammonium chloride solution to terminate the reaction, and diluted with ethyl acetate. The organic layer was separated from the aqueous layer, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:2) to obtain [4-(tert-butyldimethylsilyloxymethyl)phenyl][3-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)phenyl]methanol (0.923 g, yield 66%).

Workup

  1. additionthe flask was filled with argon
  2. additiona 1.57 mol/L n-butyl lithium-hexane solution (2.60 mL, 4.09 mmol) was added
  3. stirringby stirring at −78° C. for 1 hour
  4. customto terminate
  5. customthe reaction
  6. customThe organic layer was separated from the aqueous layer
  7. washwashed with water and saturated brine
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:2)

Sources & evidence

ORD record
ord-8ce9fbdfb6964f7c8965314fd0af75da
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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