Sodium borohydride → HCID 18923242, compound

HRID 1900015Notes

Reaction equation

HRID 1900015 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-4b764c36453f4a4db69f0a5fb86c3ea7
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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