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

HRID 1265313Notes

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-da6175a96e4141208254f44d790ebff2
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545158B2

Reaction notes

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