Potassium Fluoride → HCID 59380851, compound

HRID 2354138Notes

Reaction equation

HRID 2354138 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](=[CH:5][CH:6]=[CH:7][N: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].[F-].[K+]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[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)=[N:8][CH:7]=[CH:6][CH:5]=3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 522689Potassium Fluoride2×HCID 5910734-Formylphenylboronic Acid2×HCID 59380854HCID 59380854, compound

Product 1

HCID 59380851HCID 59380851, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-3-phenyl-1,5-naphthyridine (3-5; 103 mg, 0.43 mmole), 4-formylphenylboronic acid (77 mg, 0.51 mmole), KF (82 mg, 1.4 mmole), and Pd(PtBu3)2 (11 mg, 0.02 mmole) were combined in dry dioxane (2.5 mL). The mixture was degassed (3× pump/N2) then heated to reflux. After 18 hr the mixture was cooled to RT. 4-Formylphenylboronic acid (77 mg, 0.51 mmole), KF (82 mg, L 1.4 mmole), and Pd(PtBu3)2 (11 mg, 0.02 mmole) were added. The mixture was degassed (3× pump/N2) then heated to reflux. After 6 hr the mixture was cooled, diluted with saturated NaHCO3, and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (20% EtOAc/CHCl3) gave the title compound (3-6) as a pale yellow gum: 1H-NMR (500 MHz, CDCl3) δ 10.03 (s, 1H), 9.05 (bs, 1H), 8.48 (m, 2H), 7.82 (dd, J=1.47 and 5.13 Hz, 2H), 7.71 (m, 1H), 7.63 (d, J=8.06 Hz, 2H), 7.36-7.27 (m, 5H).

Workup

  1. customThe mixture was degassed (3× pump/N2)
  2. temperaturethen heated to reflux
  3. customThe mixture was degassed (3× pump/N2)
  4. temperaturethen heated to reflux
  5. temperatureAfter 6 hr the mixture was cooled
  6. additiondiluted with saturated NaHCO3
  7. extractionextracted with CH2Cl2 (3×)
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3bd2eb9e9690419298735a7b2963bfd1
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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