Potassium Carbonate → [2-(7-cyanomethoxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

HRID 1272216

反応式

HRID 1272216 の反応式
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]([CH3:21])([CH3:20])[CH2:9][C:10]1[C:18]2[C:13](=[C:14]([OH:19])[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:24][C:25]#[N:26].C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]([CH3:21])([CH3:20])[CH2:9][C:10]1[C:18]2[C:13](=[C:14]([O:19][CH2:24][C:25]#[N:26])[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 69519112[2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

生成物 1

HCID 69516800[2-(7-cyanomethoxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester収率 86.5%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

A mixture of [2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (15.55 g, 51.1 mmol), bromoacetonitrile (10.7 mL, 153 mmol), K2CO3 (17.78 g, 128.6 mmol) and 2-butanone is heated to reflux. After 1 hour the mixture is allowed to cool and is filtered through celite. The filtrate is concentrated to an oil which is purified by flash chromatography with CH2Cl2 followed by 5% ethyl acetate/CH2Cl2 to give 15.18 g of [2-(7-cyanomethoxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (86%). MS (ES−) m/z 342.

後処理

  1. temperatureis heated to reflux
  2. temperatureto cool
  3. filtrationis filtered through celite
  4. concentrationThe filtrate is concentrated to an oil which
  5. customis purified by flash chromatography with CH2Cl2

出典と根拠

ORDレコード
ord-cb5e15b2a9b343c98a299ba51802a753
出典データセット
uspto-grants-2007_04
特許番号
US07208505B2

関連ノート

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