Ethyl Acetate → HCID 67247681, compound

HRID 1192485Notes

Reaction equation

HRID 1192485 reaction equation
[N:1]([CH:4]([C:6]1[C:15]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([F:22])[CH:21]=2)=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1)[CH3:5])=[N+]=[N-].CP(C)C.C(OCC)(=O)C>O1CCCC1.O>[F:22][C:20]1[CH:21]=[C:16]([C:15]2[C:6]([CH:4]([NH2:1])[CH3:5])=[CH:7][CH:8]=[C:9]3[C:14]=2[N:13]=[CH:12][CH:11]=[CH:10]3)[CH:17]=[N:18][CH:19]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 86656170HCID 86656170, compound

Product 1

HCID 67247681HCID 67247681, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 7-(1-azidoethyl)-8-(5-fluoropyridin-3-yl)quinoline (0.147 g, 0.500 mmol) in tetrahydrofuran (1 mL) and water (0.360 mL) was added 1.00 M trimethylphosphine in tetrahydrofuran (0.60 mL, 0.60 mmol) at room temperature and the mixture was stirred at room temperature for 1 hour. To the mixture was added ethyl acetate and the mixture was extracted with 1 N HCl twice. The combined extracts were neutralized with solid sodium bicarbonate, and then extracted with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue showed two peaks by LCMS with the same desired mass and was used directly in next step (112 mg, 84%). LCMS calculated for C16H15FN3(M+H)+: m/z=268.1; found: 268.0.

Workup

  1. extractionthe mixture was extracted with 1 N HCl twice
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5436c937f99487784eb4fc966663fcf
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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