Potassium Phosphate, Tribasic → HCID 87416753, compound

HRID 1818634Notes

Reaction equation

HRID 1818634 reaction equation
C([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]([F:16])([F:15])[F:14])[CH:10]=2)[NH:5][C:4]=1[C:17]([OH:19])=[O:18])C.I[C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H:41]1CCCC[C@H:42]1NC>[Cu](I)I>[F:16][C:13]([F:14])([F:15])[O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[C:4]([C:17]([O:19][CH2:41][CH3:42])=[O:18])=[CH:3]2

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 53406017HCID 53406017, compound

Product 1

HCID 87416753HCID 87416753, compound

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

To a vial containing ethyl 5-trifluoromethoxyindole-2-carboxylic acid (500 mg, 1.83 mmol) were added 4-iodobenzotrifluoride (323 mg, 2.20 mmol), potassium phosphate (815 mg, 3.84 mmol), copper iodide (17.5 mg, 0.092 mmol), and trans N,N′-dimethyl-1,2-cyclohexanediamine (0.058 mL, 0.37 mmol). The resulting mixture was purged with N2, and degassed toluene (2 mL) was added. The reaction mixture was capped, placed in a 110° C. bath, and was stirred for 18 h. Upon cooling to room temperature, the mixture was filtered and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30% then 30 to 100% EtOAc in hexanes) gave the title compound: LCMS A, tr=4.28 min, m/z 418.1 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.80 (d, J=8.5 Hz, 2H), 7.60 (s, 1H), 7.48 (s, 1H), 7.47 (d, J=8.5 Hz, 2H), 7.17 (dd, J=9.0, 1.5 Hz, 1H), 7.07 (d, J=9.0 Hz, 1H), 4.25 (q, J=7.0 Hz, 2H), 1.25 (t, J=7.0 Hz, 3H).

Workup

  1. customThe resulting mixture was purged with N2
  2. customdegassed toluene (2 mL)
  3. additionwas added
  4. customThe reaction mixture was capped
  5. customplaced in a 110° C.
  6. filtrationthe mixture was filtered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel (0 to 30%

Sources & evidence

ORD record
ord-c1125906cc4a4d188b96669822cbb9a2
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

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