Sodium Carbonate → HCID 57774343, compound

HRID 1931346Notes

Reaction equation

HRID 1931346 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10]([Si:12]([C:17]#[CH:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[CH3:11].[Cl-].[Li+].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:11]=[C:10]([Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 637947(Triethylsilyl)acetyleneHCID 110760102-Amino-5-chloro-3-iodopyridine

Product 1

HCID 57774343HCID 57774343, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 40 (9.5 g, 37.3 mmol) was dissolved in 320 mL of DMF and triethylsilylacetylene (20 mL, 112 mmol), Pd2Cl2 (dppf)2 (1.52 g, 1.9 mmol), lithium chloride (1.58 g, 37.3 mmol) and 2M Na2CO3 (7.9 mL, 74.7 mL) were added and the mixture was stirred and refluxed at 90° C. for 15 h under nitrogen. Diluted with ethyl acetate-ether mixture (1:1) and the organic phase washed with water and brine then dried (Na2SO4) and concentrated in vacuo. The residue was subjected to flash chromatography (20% EtOAc/80% hexanes) to give 4.37 g (44%) of the desired product 41. 1H NMR (500 MHz, CDCl3) 9.4 (bs, 1H), 8.2 (s, 1H), 7.9 (s, 1H), 6.6 (s, 1H), 0.9 (t, 9H), 0.75 (q, 6H).

Workup

  1. washthe organic phase washed with water and brine
  2. dry with materialthen dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32d2e8cb8490402191eb7d03d4824cb2
Source dataset
uspto-grants-2012_05
Patent number
US08188281B2

Reaction notes

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