Benzyl Bromide → Ethyl 1-benzyl-5-bromo-1H-indole-2-carboxylate

HRID 346839ノート

反応式

HRID 346839 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH4+].[Cl-]>CN(C=O)C.CCOCC>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 259091Ethyl 5-Bromoindole-2-carboxylate

生成物 1

HCID 21964289Ethyl 1-benzyl-5-bromo-1H-indole-2-carboxylate収率 98.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5 g (19 mmol) of 5-bromoindol-2-carboxylic acid ethyl ester in 20 mL of anhydrous DMF was added portionwise 1.06 g (24 mmol) of NaH (55% in oil). The mixture was stirred at RT for 45 minutes, treated dropwise with 2.9 mL (24 mmol) of benzyl bromide and stirred for three hours. After addition of a saturated aqueous solution of NH4Cl and Et2O, the phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 6.7g (98%) of crude 5-bromo-1-benzylindole-2-carboxylic acid ethyl ester, orange oil, MS: 358 (MH+).

後処理

  1. stirringstirred for three hours
  2. customthe phases were separated
  3. extractionthe aqueous one was extracted with Et2O
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated

出典と根拠

ORDレコード
ord-13a9417f5bd04d2daa7c29e05bc8a8f5
出典データセット
uspto-grants-2007_02
特許番号
US07173048B2

反応ノート

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