Iodoethane → HCID 70665297, compound

HRID 1403640Notes

Reaction equation

HRID 1403640 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([NH:18][CH2:19][CH2:20][CH3:21])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:22]([O:24]C)=[O:23])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28][CH2:29]I>O1CCCC1>[CH2:28]([N:18]([CH2:19][CH2:20][CH3:21])[C:17]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:22]([OH:24])=[O:23])=[CH:12][CH:11]=2)[CH3:29]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 70664870HCID 70664870, compound

Product 1

HCID 70665297HCID 70665297, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-(propylamino)quinoxaline-6-carboxylate (70 mg, 0.21 mmol) in tetrahydrofuran (30 mL) was added sodium hydride (32 mg, 1.32 mmol) and CH3CH2I (1.5 mL), and the reaction was stirred overnight at room temperature. The reaction was then quenched with water (50 mL), adjusted to pH 5 with HCl (3N), and extracted with ethyl acetate (3×40 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the residue, which was purified by Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18, 19*50 mm 5 um; mobile phase, water with 0.03% NH3H2O and CH3CN (10% CH3CN up to 35% in 8 min); Detector, UV 220 nm] to afford 3-(ethyl(propyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a light yellow solid (45.0 mg, 62.0%).

Workup

  1. customThe reaction was then quenched with water (50 mL)
  2. extractionextracted with ethyl acetate (3×40 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the residue, which
  6. customwas purified by Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC)
  7. waitmobile phase, water with 0.03% NH3H2O and CH3CN (10% CH3CN up to 35% in 8 min)

Sources & evidence

ORD record
ord-d228ec330df24faaa482a0d7415c7bc9
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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