Cesium fluoride → HCID 178497466, compound

HRID 2085773Notes

Reaction equation

HRID 2085773 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([OH:17])[CH:13]=[CH:12]2)(=O)=O.[CH3:20][O:21][C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23].[F-].[Cs+]>COCCOC.CO.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>[OH:17][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[C:7]([C:27]3[CH:28]=[CH:29][C:24]([C:22]([O:21][CH3:20])=[O:23])=[CH:25][CH:26]=3)[CH:8]=[CH:9][CH:10]=2)[N:15]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27343694-Methoxycarbonylphenylboronic acidHCID 178527603HCID 178527603, compound

Product 1

HCID 178497466HCID 178497466, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of Example 336A (2.93 g, 10 mmol), 4-(methoxycarbonyl)phenylboronic acid (1.80 g, 10 mmol), Pd(Ph3P)4 (0.346 g, 0.3 mmol), and CsF(1.52 g, 10 mmol) in DME (60 mL) and methanol (30 mL) was heated to reflux for 18 hours and concentrated. The concentrate was dissolved in water (50 mL) and ethyl acetate (300 mL) and the organic phase was washed with water (2×50 mL) and brine (50 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate to provide the desired product. MS (APCI) m/e 280, 278 (M+H)+, (M−H)−.

Workup

  1. temperatureto reflux for 18 hours
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in water (50 mL)
  4. washethyl acetate (300 mL) and the organic phase was washed with water (2×50 mL) and brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-d1c82dca40be4d92aaa299a6bd3205f1
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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