Sodium borohydride → N-(3,5-Dichloropyridin-4-yl)-2-[1-(4-fluorobenzyl)-5-hydroxyindol-3-yl]-2-hydroxyacetamide

HRID 394573

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:31])[C:7]=1[NH:8][C:9](=[O:30])[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([OH:21])[CH:19]=2)[N:14]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH:13]=1)=[O:11].[BH4-].[Na+]>CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:31])[C:7]=1[NH:8][C:9](=[O:30])[CH:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([OH:21])[CH:19]=2)[N:14]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH:13]=1)[OH:11]

Participants

Conditions

Temperature: 20 °C

Procedure

1 g of N-(3,5-dichloropyridin-4-yl)-2-[1-(4-fluorobenzyl)-5-hydroxyindol-3-yl]-2-oxoacetamide (1; 2 mmol) are suspended in 75 ml methanol. After addition of a solution of 0.2 g of sodium borohydride in 3 ml dilute sodium hydroxide solution, the reaction mixture is stirred at 20° C. for 6 hours. After the solvent has been removed by distillation, the residue is recrystallized from 40 ml ethanol.

Workup

customAfter the solvent has been removed by distillation
customthe residue is recrystallized from 40 ml ethanol

Sources & evidence

ORD record: ord-2b9141bee01e43fab08358b3bc2e9998
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06602890B2

Linked notes

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