Sodium Carbonate → HCID 59436008, compound

HRID 1802501Notes

Reaction equation

HRID 1802501 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][NH:23][C:24](=[O:25])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(O)(/C=C/B1O[C:40](C)([CH3:42])[C:39]([CH3:45])([CH3:44])[O:38]1)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[C:6](/[CH:42]=[CH:40]/[C:39]([OH:38])([CH3:45])[CH3:44])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][NH:23][C:24](=[O:25])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11117347581802-26-8HCID 59436068HCID 59436068, compound

Product 1

HCID 59436008HCID 59436008, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-[(2,6-dichloro-4-iodophenyl)amino]pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one (Example 156, Step 1) (30 mg, 0.06 mmol) in DMF (1.5 mL) were added sodium carbonate (2 M, 0.5 mL), tetrakis(triphenylphosphine)palladium (0) (14.3 mg, 0.12 mmol), and (3E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol (13.2 mg, 0.06 mmol). The solution was degassed by bubbling nitrogen gas and heated to 80° C. overnight. After cooling to room temperature, the mixture was extracted with 3:1 CHCl3/iPrOH. The organic layers were combined, dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by column chromatography on silica gel (100% CH2Cl2 to 70% CH2Cl2/30% MeOH) afforded the title compound.

Workup

  1. customThe solution was degassed
  2. customby bubbling nitrogen gas
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture was extracted with 3:1 CHCl3/iPrOH
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography on silica gel (100% CH2Cl2 to 70% CH2Cl2/30% MeOH)

Sources & evidence

ORD record
ord-b3e952e203b54202ba22f00419086a51
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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