Sodium hydride → (E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one

HRID 1854397Notes

Reaction equation

HRID 1854397 reaction equation
[CH:1]1([C:7](=[O:17])[CH2:8]P(=O)(OCC)OCC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[S:20]([N:30]1[C:34]2=[N:35][CH:36]=[C:37]([CH:39]=O)[N:38]=[C:33]2[CH:32]=[CH:31]1)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH:1]1([C:7](=[O:17])/[CH:8]=[CH:39]/[C:37]2[N:38]=[C:33]3[CH:32]=[CH:31][N:30]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:21])=[O:22])[C:34]3=[N:35][CH:36]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11043558Diethyl (2-cyclohexyl-2-oxoethyl)phosphonateHCID 580098835-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde

Product 1

HCID 58010004(E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-oneYield 76.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl 2-cyclohexyl-2-oxoethylphosphonate (0.609 g, 2.32 mmol) in THF (10 mL) was added NaH (60% dispersion in mineral oil, 0.0664 g, 1.66 mmol). After about 30 min, a solution of 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (0.20 g, 0.64 mmol, Example #10, Step B) in THF (10 mL) was added. After about 2 h, EtOAc (50 mL) and saturated aqueous NH4Cl (50 mL) was added to the reaction mixture. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated with IPA (20 mL) to provide (E)-1-cyclohexyl-3-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)prop-2-en-1-one as a tan solid (0.20 g, 73%): LC/MS (Table 2, Method a) Rt=3.06 min; MS m/z: 410 (M+H)+.

Workup

  1. waitAfter about 2 h
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with IPA (20 mL)

Sources & evidence

ORD record
ord-38a886072d5d457a94d549f261d0455f
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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