Lithium borohydride → 6-Bromo-8-(2,6-dimethyl-4-fluorobenzylamino)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine

HRID 1386072Notes

Reaction equation

HRID 1386072 reaction equation
[Li+].[BH4-].[Br:3][C:4]1[CH:5]=[C:6]([NH:19][CH2:20][C:21]2[C:26]([CH3:27])=[CH:25][C:24]([F:28])=[CH:23][C:22]=2[CH3:29])[C:7]2[N:8]([C:10]([C:14](OCC)=[O:15])=[C:11]([CH3:13])[N:12]=2)[CH:9]=1>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]([NH:19][CH2:20][C:21]2[C:26]([CH3:27])=[CH:25][C:24]([F:28])=[CH:23][C:22]=2[CH3:29])[C:7]2[N:8]([C:10]([CH2:14][OH:15])=[C:11]([CH3:13])[N:12]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 217173256-Bromo-3-carboethoxy-8-(2,6-dimethyl-4-fluorobenzylamino)-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 217173576-Bromo-8-(2,6-dimethyl-4-fluorobenzylamino)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridineYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (70 mg) was added in portions and during 4 h to a refluxed solution of 6-bromo-3-carboethoxy-8-(2,6-dimethyl-4-fluorobenzylamino)-2-methylimidazo[1,2-a]pyridine (100 mg, 0.23 mmol) in THF. The reaction mixture was quenched by addition of diluted HCl and methylene chloride was added. The organic layer was separated, dried and evaporated in vacuo. The residue was purified by column chromatography on silica gel, using methylene chloride:ethyl acetate (100:10) as eluent to give 40 mg (44%) of the title compound.

Workup

  1. customThe reaction mixture was quenched by addition of diluted HCl and methylene chloride
  2. additionwas added
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5f7e84c156db4b3cba044e5f36916c33
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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