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

HRID 485347Notes

Reaction equation

HRID 485347 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-4d1ad4bd88ea4a33812b64cc80c5fe0c
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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