Hydrochloric Acid → 3-(4-Hydroxybutyl)-1H-indole-5-carbonitrile

HRID 628790

反応式

HRID 628790 の反応式
[CH:1]1[C:6]([C:7]#[N:8])=[CH:5][C:4]2[C:9]([CH2:12][CH2:13][CH2:14][CH2:15]N3CCN(C4C=CC5OC(C(N)=O)=CC=5C=4)CC3)=[CH:10][NH:11][C:3]=2[CH:2]=1.ClCCCC(C1C2C(=CC=C(C#N)C=2)NC=1)=[O:39].[BH4-].[Na+].Cl>C(O)(C)C>[OH:39][CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[C:4]2[C:3](=[CH:2][CH:1]=[C:6]([C:7]#[N:8])[CH:5]=2)[NH:11][CH:10]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 6918314VilazodoneHCID 102205283-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

生成物 1

HCID 121509853-(4-Hydroxybutyl)-1H-indole-5-carbonitrile

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

As per the process described in CN'932 publication, vilazodone is prepared by reacting 3-(4-chlorobutyryl)-1H-indole-5-carbonitrile with sodium borohydride in isopropanol at reflux temperature, followed by treating the reaction mass with dilute hydrochloric acid and subsequent workup and then subjecting to column chromatography purifications to produce 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile. The hydroxylbutyl intermediate obtained is then subjected to sulfonylation using a sulfonylating agent selected from p-toluenesulfonyl chloride, benzenesulfonyl chloride, methanesulfonyl chloride and trifluoromethanesulfonyl chloride to produce corresponding sulfonylated intermediate, which is then condensed with 5-(1-piperazinyl)benzofuran-2-carboxamide in acetonitrile to produce vilazodone.

後処理

  1. customis prepared
  2. temperatureat reflux temperature

出典と根拠

ORDレコード
ord-94ad5614d6ce4816a24f02076f9a69d9
出典データセット
uspto-grants-2016_04
特許番号
US09315456B2

関連ノート

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