Benzyl Bromide → Ammonium Hydroxide

HRID 1421708Notes

Reaction equation

HRID 1421708 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:39])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[N:16]=[CH:17][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:19]=3)=[CH:10][N:9]=2)[CH:7]=1.[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CC#N>[NH4+:6].[OH-:39].[CH2:40]([N:16]1[C:15]([CH2:14][C:11]2[CH:12]=[CH:13][C:8]([N:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]3=[O:39])=[N:9][CH:10]=2)=[CH:19][N:18]=[CH:17]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Product 2

HCID 14923Ammonium HydroxideYield 0.4%HCID 187797495'-(3-Benzyl-3H-imidazol-4-ylmethyl)-5-chloro-[1,2']bipyridinyl-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-chloro-5'-(1-triphenylmethyl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (0.10 g, 0.189 mmol) and benzyl bromide (0.036 g, 0.208 mmol) in CH3CN (1 mL) was heated at 50° C. for 18 h. The solvent was removed in vacuo and the residue was heated to reflux in MeOH (3 mL) for 1 h, then concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 (3 mL) and CH2Cl2 (3 mL). The organic layer was removed and the aqueous phase extracted further with CH2Cl2 (2×3 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with CH2Cl2 ; 4% MeOH; 0.4% NH4OH, to give the title compound:

Workup

  1. customThe solvent was removed in vacuo
  2. temperaturethe residue was heated
  3. temperatureto reflux in MeOH (3 mL) for 1 h
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between saturated NaHCO3 (3 mL) and CH2Cl2 (3 mL)
  6. customThe organic layer was removed
  7. extractionthe aqueous phase extracted further with CH2Cl2 (2×3 mL)
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by flash column chromatography
  12. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-dab4213a3d584a6984116775f83ac430
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

Loading…