Potassium Phosphate, Tribasic → HCID 59375395, compound

HRID 2193028Notes

Reaction equation

HRID 2193028 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=2[C:14]2[C:9](=[CH:10][CH:11]=[N:12][C:13]=2[O:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:8]=1)(=O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH:37]1(P(C2CCCCC2)C2CCCCC2)[CH2:42]CCC[CH2:38]1.C(B1OC(C)(C)C(C)(C)O1)(C)=C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH2:23]([O:22][C:13]1[N:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C:7]([C:37]([CH3:42])=[CH2:38])=[N:8]2)[CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 593755261-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate

Product 1

HCID 59375395HCID 59375395, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1-butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate (1.00 g, 2.39 mmol), potassium phosphate tribasic (1.52 g, 7.17 mmol), palladium(II) acetate (0.0540 g, 0.239 mmol), and tricyclohexylphosphine (0.134 g, 0.478 mmol) were combined in pressure vessel. Toluene (20 ml), water (6.67 ml), and isopropenylboronic acid pinacol ester (0.899 ml, 4.78 mmol) were added. The resulting suspension was purged with argon (subsurface bubbling) for 10 min. The reaction mixture was stirred in a sealed pressure vessel at 100° C. for 2.5 h. After cooling the reaction mixture was diluted with EtOAc, and washed with aqueous ammonium chloride. The organic layer was dried over sodium sulfate, filtered, and concentrated to a crude residue that was adsorbed on to silica gel and purified by column chromatography on silica gel eluting with an EtOAc/hexane gradient to afford 1-butoxy-9-fluoro-6-isopropenylbenzo[c]-1,6-naphthyridine. LRMS (ESI) calc'd for (C19H19FN2O) [M+H]+, 311.1; found 311.1.

Workup

  1. customThe resulting suspension was purged with argon (subsurface bubbling) for 10 min
  2. temperatureAfter cooling the reaction mixture
  3. additionwas diluted with EtOAc
  4. washwashed with aqueous ammonium chloride
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a crude residue that
  8. custompurified by column chromatography on silica gel eluting with an EtOAc/hexane gradient

Sources & evidence

ORD record
ord-320396cf77ba4409b270ba2aea83ec78
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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