Pyridine → HCID 178430168, compound

HRID 1864687Notes

Reaction equation

HRID 1864687 reaction equation
[O:1]([C@H:19]1[C@@H:26]2[N:22](/[C:23](=[N:27]/[C:28]3[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[C:30]([Cl:36])[C:29]=3[CH3:37])/[O:24][CH2:25]2)[CH2:21][CH2:20]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[OH:1][C@H:19]1[C@@H:26]2[N:22](/[C:23](=[N:27]/[C:28]3[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[C:30]([Cl:36])[C:29]=3[CH3:37])/[O:24][CH2:25]2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 178430169HCID 178430169, compound

Product 1

HCID 178430168HCID 178430168, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1I (29.0 mg, 0.0550 mmol) in THF (2 mL) at 0° C. was added HF/pyridine mixture (˜2.3:1, 0.120 mL) and the reaction was stirred at rt overnight. Saturated aqueous NaHCO3 was added (5 mL), and the product was extracted with EtOAc (3×5 mL). The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, then filtered and concentrated. Purification via flash chromatography (silica gel, 0-90% EtOAc in hexane) provided the title compound (10.0 mg). LCMS: niz 292 [M+H]+.

Workup

  1. extractionthe product was extracted with EtOAc (3×5 mL)
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via flash chromatography (silica gel, 0-90% EtOAc in hexane)

Sources & evidence

ORD record
ord-490c39ffd99b4effa0d2251eb0bcb3d0
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

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