Sodium borohydride → HCID 57743023, compound

HRID 1924317Notes

Reaction equation

HRID 1924317 reaction equation
COC1C=CC(CN2C3=NC=CC(CO)=C3N=C2)=CC=1.[BH4-].[Na+].[CH3:23][O:24][C:25]1[CH:49]=[CH:48][C:28]([CH2:29][N:30]2[C:34]3=[N:35][C:36]([C:44]([F:47])([F:46])[F:45])=[CH:37][C:38]([C:39](OCC)=[O:40])=[C:33]3[N:32]=[CH:31]2)=[CH:27][CH:26]=1>>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][N:30]2[C:34]3=[N:35][C:36]([C:44]([F:47])([F:45])[F:46])=[CH:37][C:38]([CH2:39][OH:40])=[C:33]3[N:32]=[CH:31]2)=[CH:48][CH:49]=1

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 57743074HCID 57743074, compoundHCID 57743081HCID 57743081, compound

Product 1

HCID 57743023HCID 57743023, compoundYield 45.3%

Procedure

This step is realized as described in example 68.5. for the synthesis of [3-(4-methoxybenzyl)-3H-imidazo[4,5-b]pyridin-7-yl]methanol x183 with the use of 3 eq of NaBH4 for 1.45 g (3.8 mmol) of ethyl 3-(4-methoxybenzyl)-5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylate x196. Purification by chromatography on silicagel affords 0.58 g of [3-(4-methoxybenzyl)-5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-7-yl]methanol x199.

Workup

  1. customPurification by chromatography on silicagel

Sources & evidence

ORD record
ord-b9e6bb1e82774de2be1f2a81070803e3
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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