Water → HCID 67246800, compound

HRID 1192483Notes

Reaction equation

HRID 1192483 reaction equation
[N:1]([CH:4]([C:6]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1)[CH3:5])=[N+]=[N-].O.CP(C)C.C(OCC)(=O)C>O1CCCC1>[F:22][C:18]1[CH:17]=[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:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 86656169HCID 86656169, compound

Product 1

HCID 67246800HCID 67246800, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 7-(1-azidoethyl)-8-(3-fluorophenyl)quinoline (0.146 g, 0.500 mmol) in tetrahydrofuran (1 mL) and water (0.360 mL, 20.0 mmol) was added 1.00 M of trimethylphosphine in tetrahydrofuran (0.600 mL, 0.600 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. LCMS calculated for C17H16FN2(M+H)+: m/z=267.1; found: 267.0.

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-62ed1007ad18415b836eaa62bd571501
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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