Cesium fluoride → HCID 54747342, compound

HRID 553537Notes

Reaction equation

HRID 553537 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:23]=[C:22]3[C:17]([C:18]([OH:30])=[C:19]([C:26]([O:28]C)=O)[C:20](=[O:25])[N:21]3[CH3:24])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[O:7])(C)(C)C.BrC1C=C2C([C:36](O)=[C:37]([C:44]([O:46]C)=[O:45])C(=O)N2C)=CC=1.C(OC(C1C=CC(B(O)O)=CC=1)=O)(C)(C)C.[F-].[Cs+]>CCOC(C)=O.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.CO>[C:44]([CH2:37][CH2:36][C:26]([C:19]1[C:20](=[O:25])[N:21]([CH3:24])[C:22]2[C:17]([C:18]=1[OH:30])=[CH:16][CH:15]=[C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:6]([OH:5])=[O:7])=[CH:9][CH:10]=1)[CH:23]=2)=[O:28])([OH:46])=[O:45]

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 2773301(4-((Tert-butoxy)carbonyl)phenyl)boronic acidHCID 59340050HCID 59340050, compoundHCID 67410169HCID 67410169, compound

Product 1

HCID 54747342HCID 54747342, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate. To a mixture of methyl 7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (Method 7) (3.82 g, 12.2 mmol), 4-(tert-butoxycarbonyl)phenylboronic acid (2.72 g, 12.2 mmol), cesium fluoride (5.58 g, 36.7 mmol), and tetrakis(triphenylphosphine)palladium [0] (0.424 g, 0.367 mmol) in a vial, was added MeOH (61 mL). The vial was sealed and heated at 80° C. for 2 hours. The reaction mixture was then cooled, diluted with 200 mL of EtOAc, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotary evaporation to give the product. The resulting product was purified via flash chromatography (silica gel) to provide the title compound as an off-white solid.

Workup

  1. customThe vial was sealed
  2. temperatureThe reaction mixture was then cooled
  3. additionadded to a separatory funnel
  4. custompartitioned with sodium bicarbonate (saturated, aqueous)
  5. washwashed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous)
  6. customseparated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated via rotary evaporation
  9. customto give the product
  10. customThe resulting product was purified via flash chromatography (silica gel)

Sources & evidence

ORD record
ord-b6868b999e1345f08a9f3686062a71f8
Source dataset
uspto-grants-2011_11
Patent number
US08048894B2

Reaction notes

Loading…