Ethyl Acetate → HCID 67247044, compound

HRID 1192477Notes

Reaction equation

HRID 1192477 reaction equation
[N:1]([CH:4]([C:6]1[C:15]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[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-].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]=[C:18]([F:23])[CH:19]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 86656166HCID 86656166, compound

Product 1

HCID 67247044HCID 67247044, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 7-(1-azidoethyl)-8-(3,5-difluorophenyl)quinoline (0.040 g, 0.13 mmol) in tetrahydrofuran (0.4 mL) and water (0.093 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (0.155 mL, 0.155 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 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 same desired mass and was used directly in next step (30 mg, 81%). LCMS calculated for C17H15F2N2(M+H)+: m/z=285.120; found: 285.0.

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-2a149861d37e4e4c8479b93f589272ba
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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