Potassium Phosphate, Tribasic → HCID 67482392, compound

HRID 1818629Notes

Reaction equation

HRID 1818629 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.I[C:17]1[CH:18]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:21][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 78518Ethyl 5-chloroindole-2-carboxylate

Product 1

HCID 67482392HCID 67482392, compound

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Conditions

Temperature
110 °C

Procedure

To a vial containing ethyl 5-chloroindole-2-carboxylate (1.50 g, 6.70 mmol), were added 3-iodobenzotrifluoride (1.16 mL, 8.10 mmol), potassium phosphate (2.98 g, 14.1 mmol), copper iodide (64.0 mg, 0.34 mmol), and 1,2-trans-N,N′-dimethylcyclohexane diamine (0.211 mL, 1.33 mmol), and the mixture was purged with N2. Anhydrous toluene (degassed via N2-sparge, 6.7 mL) was added, and the reaction vial was capped and placed in a pre-heated (110° C.) oil bath. The mixture was stirred vigorously for 18 h, then was allowed to cool to room temperature. The reaction mixture was filtered, rinsing with ethyl acetate, and the filtrate was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30%, then 30 to 100% hexanes in ethyl acetate) afforded the title compound: LCMS C, tr=2.86 min, m/z 368.1 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.76 (d, J=8.0 Hz, 1H), 7.71 (d, J=2.0 Hz, 1H), 7.66 (t, J=8.0 Hz, 1H), 7.60 (s, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.42 (s, 1H), 7.25 (dd, J=9.0, 2.0 Hz, 1H), 6.97 (d, J=9.0 Hz, 1H), 4.22 (q, J=7.0 Hz, 2H), 1.22 (t, J=7.0 Hz, 3H).

Workup

  1. customthe mixture was purged with N2
  2. additionAnhydrous toluene (degassed via N2-sparge, 6.7 mL) was added
  3. customthe reaction vial was capped
  4. temperatureto cool to room temperature
  5. filtrationThe reaction mixture was filtered
  6. washrinsing with ethyl acetate
  7. concentrationthe filtrate was concentrated in vacuo
  8. customPurification by flash chromatography on silica gel (0 to 30%

Sources & evidence

ORD record
ord-2073b75c0dd04f9e880b8a5d1833f194
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

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