Sodium Carbonate → HCID 21103206, compound

HRID 1354807Notes

Reaction equation

HRID 1354807 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[C:12]1([C:11]2[C:2]([C:23]3[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=3)=[N:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][N:5]=3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 15262902HCID 15262902, compound

Product 1

HCID 21103206HCID 21103206, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-3-phenyl-1,8-naphthyridine (Rani, H. S.; Mogilaiah, K.; Sreenivasulu, B. Indian J. Chem. Sect. B. 1996, 35, 106; 154 mg, 0.64 mmole), 4-formylphenylboronic acid (144 mg, 0.96 mmole), 2 M Na2CO3 (0.64 mL, 1.28 mmole), and Pd(PPh3)4 (37 mg, 0.03 mmole) were combined in dioxane (3 mL) in a sealed microwave vessel. The mixture was degassed (3× vacuum/N2) then microwave irridiated at 150° C. for 30 min. The mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (60% EtOAc/hexanes) gave the title compound as a yellow foam (10-1): 1H-NMR (500 MHz, CDCl3) δ 10.02 (s, 1 H), 9.19 (dd, J=1.95, 2.20 Hz, 1 H), 8.28 (dd, J=1.95, 6.35 Hz, 1 H), 8.26 (s, 1 H), 7.79 (d, J=8.30 Hz, 2 H), 7.73 (d, J=8.05 Hz, 2 H), 7.57 (m, 1H), 7.35 (m, 2H), 7.27 (m, 3 H).

Workup

  1. customThe mixture was degassed (3× vacuum/N2)
  2. additionThe mixture was diluted with H2O
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1bca1c1e5aa94793b8103115ef9e7710
Source dataset
uspto-grants-2007_05
Patent number
US07223738B2

Reaction notes

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