Water → HCID 136146135, compound

HRID 2423397Notes

Reaction equation

HRID 2423397 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O>[OH:34][C:31]1[CH:32]=[CH:33][C:28]([C:2]2[CH:11]=[C:10]3[C:5]([C:6]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[N:9]3)=[CH:4][CH:3]=2)=[CH:29][CH:30]=1

Participants

9

Reactant 5

HCID 962WaterHCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 67245888Dimethyl 7-bromoquinoline-2,4-dicarboxylate

Product 1

HCID 136146135HCID 136146135, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 150 mg (0.46 mmol) of dimethyl 7-bromo-2,4-quinolinedicarboxylate synthesized according the procedure of Corey, E. J. and Tramontano, A., 1981 J. Am. Chem. Soc. 103:5599-5600 and Carrigan, C. N., et al, 1999 Bioorg. Med. Chem. Lett. 9:2607-2612, 153 mg (0.69 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 5 mg (0.02 mmol) of palladium acetate, 12 mg (0.05 mmol) of triphenylphosphine, 345 mg (1.62 mmol) of K3PO4, and 40 μL (2.31 mmol) of H2O in 3 mL of dioxane were stirred at 60° C. for 1.5 hr. EtOAc was then added and the solution washed with H2O. The aqueous layer was extracted with EtOAc and then the combined organics were washed with brine and concentrated. A small amount of cold EtOAc was added to the residue and the solids were collected by suction filtration, washed with cold EtOAc then dried to yield 79 mg (51%) of dimethyl 7-(4-hydroxyphenyl)-2,4-quinolinedicarboxylate as a brown solid. 1H NMR (400 MHz, CDCl3): δ 9.79 (s, 1H), 8.72 (d, J=9 Hz, 1H), 8.41-8.38 (m, 2H), 8.17 (d, J=9 Hz, 1H), 7.77 (d, J=8 Hz, 2H), 6.91 (d, J=8 Hz, 2H), 4.00 (s, 3H), 3.97 (s, 3H). ESI-LCMS m/z 338 (M+H)+.

Workup

  1. customsynthesized
  2. washthe solution washed with H2O
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organics were washed with brine
  5. concentrationconcentrated
  6. additionA small amount of cold EtOAc was added to the residue
  7. filtrationthe solids were collected by suction filtration
  8. washwashed with cold EtOAc
  9. customthen dried

Sources & evidence

ORD record
ord-1eabd97b8e694b49b19102313482f6aa
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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