Triethyl 2-phosphonopropionate → 3-[2-(ethoxycarbonyl)prop-1-enyl]-N-(3-pyridyl)indole

HRID 485347노트

반응식

HRID 485347 반응식
C([N-]C(C)C)(C)C.[Li+].[CH3:9][CH2:10][O:11][C:12]([CH:14](P(OCC)(OCC)=O)[CH3:15])=[O:13].[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([CH:39]=O)=[CH:31]2)[CH:25]=1>O1CCCC1>[CH2:10]([O:11][C:12]([C:14]([CH3:15])=[CH:39][C:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:30]([C:26]2[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=2)[CH:31]=1)=[O:13])[CH3:9]

참가 물질

5

반응물 3

HCID 107155Triethyl 2-phosphonopropionateHCID 2724682Lithium diisopropylamideHCID 13490349HCID 13490349, 화합물

생성물 1

HCID 539181563-[2-(ethoxycarbonyl)prop-1-enyl]-N-(3-pyridyl)indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of lithium diisopropylamide (from 1.4 ml of diisopropylamine and 6.3 ml of 1.6M n-butyllithium in hexane) in 25 ml of dry tetrahydrofuran under nitrogen is cooled to -70° and 2.14 ml of triethyl 2-phosphonopropionate is added dropwise. The reaction mixture is stirred for 20 minutes at -70° and 2.0 g of N-(3-pyridyl)indole-3-carboxaldehyde is added. The reaction is allowed to warm to room temperature for 14 hours. The solvent is evaporated and the residue is partitioned between 20 ml of half saturated ammonium chloride solution and 30 ml of methylene chloride. The organic phase is separated, dried over sodium sulfate and evaporated to a solid which is recrystallized from methanol to yield 3-[2-(ethoxycarbonyl)prop-1-enyl]-N-(3-pyridyl)indole, m.p. 97°-99°.

후처리

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between 20 ml of half saturated ammonium chloride solution and 30 ml of methylene chloride
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated to a solid which
  6. customis recrystallized from methanol

출처 및 근거

ORD 기록
ord-4d1ad4bd88ea4a33812b64cc80c5fe0c
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04536505

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