Pyridine → HCID 57504573, compound

HRID 1098079Notes

Reaction equation

HRID 1098079 reaction equation
C(Cl)(=O)C(Cl)=O.[Si:7]([O:14][C@H:15]([CH2:26][CH3:27])[C:16]([O:18][Si](C(C)(C)C)(C)C)=O)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].N1C=CC=CC=1.[NH2:34][C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][N:36]=1>C(Cl)Cl.CN(C=O)C.O>[Si:7]([O:14][C@H:15]([CH2:26][CH3:27])[C:16]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][N:36]=1)=[O:18])([C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:8])[CH3:9]

Participants

8

Reactant 4

HCID 1049PyridineHCID 153482-Amino-5-methylpyridineHCID 65578Oxalyl chlorideHCID 57438624HCID 57438624, compound

Product 1

HCID 57504573HCID 57504573, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (1.32 g, 10.43 mmol was added slowly to a stirred solution of tert-butyl(dimethyl)silyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}butanoate (Step 1) (2.77 g, 8.69 mmol) in DCM (10 mL) and DMF (three drops). After 1 h at ambient temperature, gas evolution had subsided and the reaction mixture was concentrated in vacuo to remove excess oxalyl chloride. The residue was dissolved in DCM (10 mL) and pyridine (0.89 g, 11.30 mmol) and 2-amino-5-picoline (1.03 g, 9.56 mmol) were added. The reaction mixture was kept at ambient temperature for 2 hrs. Water was added and the two phases were separated. The aqueous phase was extracted with DCM. The organic extracts were combined and washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with heptane/EtOAc:5/2) to give the title compound as a colourless oil (2.0 g). 1H NMR (500 MHz, CDCl3) δ 8.91 (br s, 1H), 8.15 (d, 2H), 7.53 (m, 1H), 4.26 (t, 1H), 2.31 (s, 3H), 1.85 (m, 2H), 0.96 (m, 12H), 0.17 (m, 6H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto remove excess oxalyl chloride
  3. dissolutionThe residue was dissolved in DCM (10 mL)
  4. waitThe reaction mixture was kept at ambient temperature for 2 hrs
  5. customthe two phases were separated
  6. extractionThe aqueous phase was extracted with DCM
  7. washwashed with water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified with column chromatography (silica gel, eluting with heptane/EtOAc:5/2)

Sources & evidence

ORD record
ord-bdb60ab9823d4647938de5eebf9bd17a
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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