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

HRID 1724026노트

반응식

HRID 1724026 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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 6.7 g (98%) of crude 5-bromo-1-benzylindole-2-carboxylic acid ethyl ester, orange oil, MS: 358 (MH+).

후처리

  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

출처 및 근거

ORD 기록
ord-812bf6aa613041aea4411a5ab7c9bd5a
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485652B2

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