Nitrogen → HCID 11144213, compound

HRID 1596045Notes

Reaction equation

HRID 1596045 reaction equation
[C:1]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)(=[O:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].N#N>O.C(OCC)(=O)C.CC(O)=O.C1(C)C=CC=CC=1.CCO>[C:1]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:25]2[CH:24]=[CH:23][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:27][CH:26]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

10

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 12166960HCID 12166960, compound

Product 1

HCID 11144213HCID 11144213, compoundYield 88.3%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 9A (3.10 g, 9.22 mmol), 4-trifluoromethoxyphenylboronic acid (2.13 g, 10.14 mmol), absolute EtOH (15 mL), 2 M aqueous Na2CO3 (9.22 mL, 18.44 mmol), and toluene (65 mL) was sparged with N2, treated with tetrakis(triphenylphosphine)paladium (0) (538 mg, 0.461 mmol), and heated at reflux for 1.25 hours. The reaction mixture was cooled, diluted with H2O (50 mL) and ethyl acetate (100 mL), and acidified to pH 3 with HOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered, and concentrated. Purification on silica gel with a gradient of CH2Cl2 to 2% MeOH/Cf 2CH2 provided 3.40 g (88%) of the desired compound as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.25 hours
  3. temperatureThe reaction mixture was cooled
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification on silica gel with a gradient of CH2Cl2 to 2% MeOH/Cf

Sources & evidence

ORD record
ord-78278c5f380a496887a8888f4f3043b6
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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