Triethylamine → HCID 53373582, compound

HRID 468000Notes

Reaction equation

HRID 468000 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:12][CH2:11][O:10][B:9]([OH:13])[C:8]=2[CH:14]=1)([O-])=O.CCN(CC)CC.[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[C:25]([C:32]([F:35])([F:34])[F:33])[CH:24]=1>C1COCC1.CCOC(C)=O.[Pd]>[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:1][C:4]2[CH:5]=[CH:6][C:7]3[CH2:12][CH2:11][O:10][B:9]([OH:13])[C:8]=3[CH:14]=2)=[O:28])=[C:25]([C:32]([F:33])([F:34])[F:35])[CH:24]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 67406031HCID 67406031, compound

Product 1

HCID 53373582HCID 53373582, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-nitro-3,4-dihydro-benzo[c][1,2]oxaborinin-1-ol (100 mg, 0.52 mmol) in THF (10 mL) was passed through H-cube equipped with a 10% Pd/C cartridge. The collected light yellow solution was immediately treated with Et3N (144 μL, 2.0 mmol, 2.0 eq.), followed by 4-fluoro-2-trifluoromethyl-benzoyl chloride (94 μL, 0.62 mmol, 1.2 eq.). The resulting mixture was stirred at room temperature overnight. The reaction solution was diluted with EtOAc (20 mL), washed with 1N HCl (10 mL), H2O (10 mL), brine (10 mL) and then dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure and the crude material was applied to silica chromatography eluting with MeOH/DCM (0:100 to 10:90) to give the title compound as a white solid. LCMS (M/Z): 354 (M+H); 1H NMR (DMSO-d6) δ: 10.43 (s, 1H), 8.40 (s, 1H), 7.89 (d, J=2.3 Hz, 1H), 7.75 (dt, J=5.9, 2.9 Hz, 2H), 7.58-7.67 (m, 2H), 7.15 (d, J=8.2 Hz, 1H), 4.03 (t, J=5.9 Hz, 2H), 2.80 (t, J=5.8 Hz, 2H).

Workup

  1. customThe collected light yellow solution
  2. washwashed with 1N HCl (10 mL), H2O (10 mL), brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washeluting with MeOH/DCM (0:100 to 10:90)

Sources & evidence

ORD record
ord-f682561f42734e2e935253776420e471
Source dataset
uspto-grants-2014_01
Patent number
US08623911B2

Reaction notes

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