(2-(Dimethylamino)ethyl)triphenylphosphonium bromide → 3-(3-dimethylaminopropenyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 24335

反応式

HRID 24335 の反応式
C([Li])CCC.[Br-].[CH3:7][N:8]([CH3:30])[CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(NCC)C.[Li].[CH2:37]([O:39][C:40]([C:42]1[NH:43][C:44]2[C:49]([C:50]=1[CH:51]=O)=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])[CH3:38]>C1COCC1>[CH2:37]([O:39][C:40]([C:42]1[NH:43][C:44]2[C:49]([C:50]=1[CH:51]=[CH:10][CH2:9][N:8]([CH3:30])[CH3:7])=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])[CH3:38]

参加物

6

反応物 4

HCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 5107764ethyl 3-formyl-1H-indole-2-carboxylateHCID 45051810Lithium diethylamineHCID 178418339Butyllithium

生成物 1

HCID 543568283-(3-dimethylaminopropenyl)-1H-indole-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Butyllithium (1.1 equiv.) was added to a suspension of (2-dimethylaminoethyl)triphenylphosphonium bromide in THF (0.2 M) at 0° C. After stirring for 30 minutes, lithium diethylamine (1.1 equiv.) was added dropwise followed by the cold suspension of 3-formyl-1H-indole-2-carboxylic acid ethyl ester (3.96 g, 18.2 mmol) in THF. The resulting orange suspension was stirred for 18 hours. The reaction was then quenched with saturated ammonium chloride and extracted with 10% MeOH in DCM. The organic layer was washed with saturated sodium bicarbonate, dried and concentrated to give 3-(3-dimethylaminopropenyl)-1H-indole-2-carboxylic acid ethyl ester as a brownish-red waxy solid.

後処理

  1. stirringThe resulting orange suspension was stirred for 18 hours
  2. customThe reaction was then quenched with saturated ammonium chloride
  3. extractionextracted with 10% MeOH in DCM
  4. washThe organic layer was washed with saturated sodium bicarbonate
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-bef9feba2e844741aa8e3640f2b05a5a
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

関連ノート

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