Sodium Carbonate → HCID 86754083, compound

HRID 1415695Notes

Reaction equation

HRID 1415695 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]2=[N:14][C:15]3[C:20]([C:21](=[O:22])[N:12]2[CH:11]=[CH:10][CH:9]=1)=[CH:19][C:18](I)=[CH:17][CH:16]=3)=[O:7].[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]2=[N:14][C:15]3[CH:16]=[CH:17][CH:18]([C:27]4[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=4)[CH2:19][C:20]=3[C:21](=[O:22])[N:12]2[CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 11048376HCID 11048376, compound

Product 1

HCID 86754083HCID 86754083, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-[2-(dimethylamino)ethyl]-2-iodo-11-oxo-11H-pyrido[2,1-b]quinazoline-6-carboxamide (100 mg), 3-pyridinyl-boronic acid (225.41 mg), tetrakis(tri-phenylphosphine)palladium(0) (66.22 mg) and sodium carbonate (0.57 ml of 2 M (1.15 mmol)) was heated in an oil bath at 120° C.-125° C. for 45 minutes. The reaction mixture was cooled to room temperature, diluted with water (30 ml), and extracted with CH2Cl2 (3×30 ml). Combined organic phases were washed with brine (50 ml), dried with MgSO4, filtered and concentrated in vacuo. The residue was purified on SiO2 (50 g; gradient elution with 10-30% MeOH/CHCl3) to give the desired product (66 mg).

Workup

  1. temperaturewas heated in an oil bath at 120° C.-125° C. for 45 minutes
  2. extractionextracted with CH2Cl2 (3×30 ml)
  3. washCombined organic phases were washed with brine (50 ml)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on SiO2 (50 g; gradient elution with 10-30% MeOH/CHCl3)

Sources & evidence

ORD record
ord-aaa8d1e01ebc4be1bdbc3016606c5cad
Source dataset
uspto-grants-1999_06
Patent number
US05908840

Reaction notes

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