Sodium borohydride → HCID 57742987, compound

HRID 2043681Notes

Reaction equation

HRID 2043681 reaction equation
[Br:1][C:2]1[C:3]([C:20](OC)=[O:21])=[C:4]2[N:10]=[CH:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:5]2=[N:6][CH:7]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[C:3]([CH2:20][OH:21])=[C:4]2[N:10]=[CH:9][N:8]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57743086HCID 57743086, compound

Product 1

HCID 57742987HCID 57742987, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 6-bromo-3-(4-methoxybenzyl)-3H-imidazo[4,5-b]pyridine-7-carboxylate x210 (1.2 g, 3.19 mmol) is dissolved in absolute ethanol. NaBH4 (0.36 g, 3 eq, 9.57 mmol) is added at 5° C. under stirring. The cooling bath is removed after 4 h, and the reaction mixture is allowed to heat up to room temperature. The stirring is continued at this temperature for 20 h. The reaction mixture is evaporated in the vacuum of a rotary evaporator at 35° C., and the residue is partitioned in ethyl acetate/saturated aqueous NaHCO3 mixture. The organic layer is dried with anhydrous sodium sulfate and evaporated. The crude product is purified by chromatography on silicagel (dichloromethane/methanol) to afford 0.72 g of [6-bromo-3-(4-methoxybenzyl)-3H-imidazo[4,5-b]pyridin-7-yl]methanol x211.

Workup

  1. customThe cooling bath is removed after 4 h
  2. customThe reaction mixture is evaporated in the vacuum of a rotary evaporator at 35° C.
  3. customthe residue is partitioned in ethyl acetate/saturated aqueous NaHCO3 mixture
  4. dry with materialThe organic layer is dried with anhydrous sodium sulfate
  5. customevaporated
  6. customThe crude product is purified by chromatography on silicagel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-8fb037eb548e41c893dcc42e39661609
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

Loading…