Cesium carbonate → HCID 67445522, compound

HRID 2194876Notes

Reaction equation

HRID 2194876 reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9]C)=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:17][O:18][CH2:19][C:20]#[CH:21]>C(#N)C.C(OCC)C>[CH3:9][O:8][C:7]1[C:2]([C:21]#[C:20][CH2:19][O:18][CH3:17])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 693933-MethoxypropyneHCID 122934752-chloro-3-ethoxypyridine

Product 1

HCID 67445522HCID 67445522, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of commercially available 2-chloro-3 ethoxy pyridine (1 eq.) in acetonitrile (1.9M) was added PdCl2(CH3CN)2 (0.015 eq.), Cs2CO3 (2.4 eq.) and 2-(dicyclohexylphosphino)-2′-6′-dimethoxy-1-1′-biphyl (S—PHOS; 0.044 eq.). The suspension was sonicated for 5 min then 3-methoxyprop-1-yne (1.7 eq.) was added. The final mixture was stirred 12 h at 100° C., cooled down to room temperature, diluted with diethylether. The organic fraction was washed with water, brine, dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel, eluting with CH2Cl2/Acetone 5% afforded the desired compound.

Workup

  1. customThe suspension was sonicated for 5 min
  2. washThe organic fraction was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel
  7. washeluting with CH2Cl2/Acetone 5%

Sources & evidence

ORD record
ord-80f3b66e0ada4502a9898ea980fe2776
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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