Sodium Carbonate → HCID 178488525, compound

HRID 2252301Notes

Reaction equation

HRID 2252301 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([OH:18])[C:11]3[CH:12]=[CH:13][CH:14]=[N:15][C:16]=3[CH:17]=2)=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>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>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]=[C:10]([OH:18])[C:11]4[CH:12]=[CH:13][CH:14]=[N:15][C:16]=4[CH:17]=3)=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 178517416HCID 178517416, compound

Product 1

HCID 178488525HCID 178488525, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 7-(4-bromophenyl)-[1,6]-naphthyridin-5-ol (0.135 g, 0.45 mmol)) in DMF (4 mL), was added tetrakis(triphenylphosphine)palladium (0.025 g, 0.02 mmol). After 15 minutes, 4-methoxyphenylboronic acid (0.090 g, 0.60 mmol) and sodium carbonate (2 M aqueous solution, 0.5 mL, 1 mmol) was added. The mixture was heated to 100° C. for 12 hours and then cooled to room temperature. The white solid was collected by filtration and washed with water to afford the title compound (0.110 g).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe white solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-c2ecc56d96a044d3a4046ba616cd37ce
Source dataset
uspto-grants-2008_01
Patent number
US07321041B2

Reaction notes

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