Hydrochloric Acid → ethyl 5-ethynyl-3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-1H-indole-2-carboxylate

HRID 271734

반응식

HRID 271734 반응식
ClCCN1CCCC1.Cl.[CH3:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[C:21][Si](C)(C)C)[CH:18]=2)[N:13]([CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:12]=1[C:33]([O:35][CH2:36][CH3:37])=[O:34].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1)[C:12]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:11]2[CH3:10])#[CH:21]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 816691-(2-Chloroethyl)pyrrolidineHCID 69075563ethyl 3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-5-trimethylsilanylethynyl-1H-indole-2-carboxylate

생성물 1

HCID 86594685ethyl 5-ethynyl-3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-1H-indole-2-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

Under an argon atmosphere 562 mg (3.3 mmol) 1-(2-chloro-ethyl)-pyrrolidine (used as the hydrochloride) are added to a suspension of 900 mg (3.0 mmol) ethyl 3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-5-trimethylsilanylethynyl-1H-indole-2-carboxylate and 457 mg (3.3 mmol) K2CO3 in 10 mL DMF and the reaction mixture is stirred for 42 h at 60° C. It is diluted with water, extracted exhaustively with EtOAc, the combined organic phases are washed with water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1).

후처리

  1. extractionextracted exhaustively with EtOAc
  2. washthe combined organic phases are washed with water
  3. dry with materialdried over Na2SO4
  4. customis purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1)

출처 및 근거

ORD 기록
ord-a828ffcc3fa44e938eace57f9a6f232d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452911B2

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