Sodium borohydride → HCID 57742987, compound

HRID 1896458Notes

Reaction equation

HRID 1896458 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-06d4dc7bb43943b2879dfc574307a939
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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