2,6-Lutidine → HCID 69425288, compound

HRID 2104531Notes

Reaction equation

HRID 2104531 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)CCCCCCCCCCCCC.N1C(C)=CC=CC=1C.[C:34]([C:42]1[CH:43]=[N:44][C:45]2[C:50]([C:51]=1[C:52]1[CH:53]=[C:54]([NH:58]CC3C=CC(CC([O-])=O)=CC=3)[CH:55]=[CH:56][CH:57]=1)=[CH:49][CH:48]=[CH:47][C:46]=2[C:70]([F:73])([F:72])[F:71])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Cu+2].C1(C)C=CC=CC=1>[NH:58]([C:54]1[CH:53]=[C:52]([C:51]2[C:50]3[C:45](=[C:46]([C:70]([F:73])([F:71])[F:72])[CH:47]=[CH:48][CH:49]=3)[N:44]=[CH:43][C:42]=2[C:34]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:41])[CH:57]=[CH:56][CH:55]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 79372,6-LutidineHCID 11005Myristic AcidHCID 66827Phenylboronic AcidHCID 86598749HCID 86598749, compound

Product 1

HCID 69425288HCID 69425288, compoundYield 118.6%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenylboronic acid (0.12 g, 1.0 mmol), Cu(OAc)2 (0.036 g, 0.2 mmol), and myristic acid (0.046 g, 0.2 mmol) were combined in a 100-mL round-bottom flask with a large stir bar. A rubber septum was attached, and dry toluene (2 mL), 2,6-lutidine (0.116 mL, 1.0 mmol), and {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate (0.045 g, 0.09 mmol) were successively added. The resulting mixture was stirred at a high rate for 24 h, diluted with ethyl acetate (10 mL), filtered through a plug of silica gel, and then purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min). The product was collected based on UV absorption and concentrated to give the title compound as a yellow solid (0.05 g, 94%). MS (ESI) m/z 469; MS (ESI) m/z 467; HRMS: calcd for C29H19F3N2O, 468.1449; found (ESI, [M−H]−), 467.1362; Anal. Calcd for C29H19F3N2O: C, 74.35; H, 4.09; N, 5.98. Found: C, 74.27; H, 3.72; N, 5.82.

Workup

  1. filtrationfiltered through a plug of silica gel
  2. custompurified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min)
  3. customThe product was collected
  4. custombased on UV absorption
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-30a9a24fdccc4c96ba3bdddd956b5c42
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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