Indole-5-carbonitrile → 3-(4-hydroxybutanoyl)-1H-indole-5-carbonitrile

HRID 628792

Reaction equation

HRID 628792 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[NH:8][CH:7]=1.C(C1C=C2C(=CC=1)NC=C2)#N.ClCCCC(Cl)=[O:33].[Cl-].[Al+3].[Cl-].[Cl-]>>[OH:1][CH2:2][CH2:3][CH2:4][C:5]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[NH:8][CH:7]=1)=[O:33]

Participants

5

Reactant 4

HCID 27513Indole-5-carbonitrileHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 121509853-(4-Hydroxybutyl)-1H-indole-5-carbonitrile

Product 1

HCID 727102233-(4-hydroxybutanoyl)-1H-indole-5-carbonitrile

Procedure

The present inventors have further surprisingly and unexpectedly found that 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile intermediate can be prepared, in high purity and with high yield, by reacting 5-cyanoindole with 4-chlorobutyryl chloride in the presence of aluminium chloride to produce an intermediate compound, followed by reacting the compound with an aqueous alcohol to produce 3-(4-hydroxybutyryl)-1H-indole-5-carbonitrile, which is then reduced with sodium cyanoborohydride in the presence of hydrochloric acid and water in acetonitrile solvent to produce 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile.

Workup

  1. customcan be prepared, in high purity and with high yield
  2. customto produce an intermediate compound

Sources & evidence

ORD record
ord-710fbf00b52a4cb6b7e7a7fd84c93967
Source dataset
uspto-grants-2016_04
Patent number
US09315456B2

Linked notes

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