Water → HCID 58368544, compound

HRID 1192575Notes

Reaction equation

HRID 1192575 reaction equation
[N:1]([CH:4]([C:6]1[CH:7]=[C:8]([C:23]#[N:24])[C:9]2[CH:10]=[CH:11][CH:12]=[N:13][C:14]=2[C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)[CH3:5])=[N+]=[N-].O.CP(C)C.C(OCC)(=O)C>O1CCCC1>[NH2:1][CH:4]([C:6]1[CH:7]=[C:8]([C:23]#[N:24])[C:9]2[CH:10]=[CH:11][CH:12]=[N:13][C:14]=2[C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 58368556HCID 58368556, compound

Product 1

HCID 58368544HCID 58368544, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 7-(1-azidoethyl)-8-(3-fluorophenyl)quinoline-5-carbonitrile (0.020 g, 0.063 mmol) in tetrahydrofuran (0.2 mL) and water (0.0455 mL, 2.52 mmol) was added 1.0 M trimethylphosphine in tetrahydrofuran (0.076 mL, 0.076 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 two times. 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 LCMS of the crude, showed two peaks with the same desired mass, and was used directly in the next step (18 mg, 98%). LCMS calculated for C18H15FN3 (M+H)+: m/z =292.1; Found: 292.1.

Workup

  1. extractionthe mixture was extracted with 1 N HCl two times
  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-779a28a173d74d739f23cb14f1b31cd4
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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