Sodium hydride → (1-carbamoyl-2-methyl-1H-indol-3-yl)-acetic acid ethyl ester

HRID 1527200ノート

反応式

HRID 1527200 の反応式
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH3:15])[CH3:2].[H-].[Na+].ClS([N:23]=[C:24]=[O:25])(=O)=O>>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:24](=[O:25])[NH2:23])[C:7]=1[CH3:15])[CH3:2]

参加物

4

反応物 3

HCID 24758Sodium hydrideHCID 70918Chlorosulfonyl isocyanateHCID 324307Ethyl 2-methyl-3-indoleacetate

生成物 1

HCID 68283853(1-carbamoyl-2-methyl-1H-indol-3-yl)-acetic acid ethyl ester

実験手順

The title compound was prepared in a similar manner as described in Scheme A8 Step A starting from (2-methyl-1H-indol-3-yl)-acetic acid ethyl ester [21909-49-9] (1.20 g, 5.52 mmol), NaH (60% in mineral oil, 331 mg, 8.28 mmol) and chlorosulfonylisocyanate (0.959 mL, 11.1 mmol). Purification by flash column chromatography on silica gel (EtOAc/c-hexane 1:4 to 1:1) afforded a yellowish solid. TLC, Rf (EtOAc/c-hexane 1:1)=0.31; MS: 261 [M+H]+; tR (HPLC conditions b) 3.54 min.

後処理

  1. customPurification by flash column chromatography on silica gel (EtOAc/c-hexane 1:4 to 1:1)
  2. customafforded a yellowish solid
  3. customtR (HPLC conditions b) 3.54 min.

出典と根拠

ORDレコード
ord-0738f16fb56e4d67a76ba2accc8a5b19
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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