Sodium borohydride → HCID 18923242, compound

HRID 1290199Notes

Reaction equation

HRID 1290199 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([C:20](=[O:27])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:15][C:14]=3[Cl:28])[C:5]2=[N:4][C:3]=1[CH3:29].[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:14]([Cl:28])=[CH:15][C:16]([CH:20]([OH:27])[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:17][C:18]=3[Cl:19])[C:5]2=[N:4][C:3]=1[CH3:29]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18923252HCID 18923252, compound

Product 1

HCID 18923242HCID 18923242, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-bromo-8-(2,6-dichloro-4-benzoylbenzyloxy)-2-methylimidazo[1,2-a]pyridine (80 mg), sodium borohydride (18.5 mg) and ethanol (2 ml) was stirred at ambient temperature for 1 hour. The reaction mixture was partitioned between dichloromethane and water and the aqueous layer was extracted with dichloromethane twice. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from diethyl ether to give 3-bromo-8-[2,6-dichloro-4-(α-hydroxybenzyl)benzyloxy]-2-methylimidazo[1,2-a]pyridine (73 mg) as crystals.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. extractionthe aqueous layer was extracted with dichloromethane twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-bf34446569bd4edfa0b9a11b1c3c21b6
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

Loading…