Triethylamine → HCID 25224408, compound

HRID 1672426Notes

Reaction equation

HRID 1672426 reaction equation
FC(F)(F)S(O[C:7]1[C@H:8]([CH3:20])[CH2:9][N:10]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:11][CH:12]=1)(=O)=O.C([N:25]([CH2:28]C)[CH2:26][CH3:27])C.[F:30][C:31]([F:40])([F:39])[C:32]1[CH:38]=CC(N)=[CH:34][CH:33]=1.[C]=[O:42]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:19][C:18]1[C:13]([N:10]2[CH2:11][CH:12]=[C:7]([C:28]([NH:25][C:26]3[CH:27]=[CH:38][C:32]([C:31]([F:40])([F:39])[F:30])=[CH:33][CH:34]=3)=[O:42])[C@H:8]([CH3:20])[CH2:9]2)=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 86628447HCID 86628447, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 25224408HCID 25224408, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of palladium (II) acetate (0.065 g, 0.29 mmol), the product from Example 2F (1.03 g, 2.90 mmol), triethylamine (0.293 mg, 2.90 mmol), 2-dicyclohexylphosphine-2′-(N,N-dimethylamino)biphenyl (0.228 g, 0.579 mmol) and p-trifluoromethylaniline (0.933 g, 5.79 mmol) in N,N-dimethylformamide (20 mL) was placed under 1 atmosphere of carbon monoxide and stirred at room temperature for 2 hours. The reaction mixture was concentrated to approximately, poured into of ethyl acetate, washed with saturated sodium bicarbonate, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (gradient elution from 0% to 20% ethyl acetate-[50% CH2Cl2-hexane] to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.19 (dd, 1H, J=4.7, 1.7 Hz), 7.71 (d, 2H, J=8.5 Hz), 7.62 (dd, 1H, J=7.8, 1.7 Hz), 7.60 (d, 2H, J=8.5 Hz), 6.86 (dd, 1H, J=7.8, 4.7 Hz), 6.61 (dd, 1H, J=3.1, 3.1 Hz), 4.19-3.96 (m, 2H), 3.63 (dd, 1H, J=12.5, 4.1 Hz), 3.35 (dd, 1H, J=12.5, 4.1 Hz), 3.14-3.02 (m, 1H), 1.29 (d, 3H, J=7.1 Hz); MS (DCI/NH3) m/e 396 (M+H)+; [α]23D +37.2° (c 1.0, CH3OH).

Workup

  1. concentrationThe reaction mixture was concentrated to approximately,
  2. additionpoured into of ethyl acetate
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (
  7. washgradient elution from 0% to 20% ethyl acetate-[50% CH2Cl2-hexane]

Sources & evidence

ORD record
ord-c054e910dd614ea9bc4bf0b511f147cd
Source dataset
uspto-grants-2011_08
Patent number
US07998982B2

Reaction notes

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