Potassium Phosphate, Tribasic → [4-(3-Hydroxyphenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

HRID 2104504Notes

Reaction equation

HRID 2104504 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)=O.[OH:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[OH:31][C:32]1[CH:33]=[C:34]([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:19])([F:18])[F:20])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:28])[CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 160903243-Benzoyl-8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate

Product 1

HCID 11773771[4-(3-Hydroxyphenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)MethanoneYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-benzoyl-8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate (1.6 g, 3.6 mmol), 3-hydroxyphenylboronic acid (0.60 g, 4.3 mmol), and K3PO4 (3.0 g) in dioxane (50 ml) was heated to reflux. After, 4 hr, the reaction was cooled, filtered, concentrated to give a solid which was triturated with 10% EtOAc/hexane to give a white solid (1.2 g Yield=86%); MS (ESI) m/z 394 ([M+H]+; 1H NMR (DMSO) δ 9.54 (s, 1H), 9.11 (s, 1H), 8.339 (d, 1h, J=7.0 Hz), 8.01(d, 1H, J=8.0 Hz), 7.83-7.79 (m, 1H), 7.64-7.61 (m, 2h), 7.55-7.51 (m, 1H), 7.39 (t, 2H, J=7.8 Hz), 7.13 (t, 1H, =7.8 Hz), 6.72-6.68 (m, 3H); Anal. Calcd for C23H14F3NO2: C, 70.23; H, 3.59; N, 3.56. Found: C, 69.67; H, 3.43; N, 3.51.

Workup

  1. temperatureAfter, 4 hr, the reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customto give a solid which
  5. customwas triturated with 10% EtOAc/hexane
  6. customto give a white solid (1.2 g Yield=86%)

Sources & evidence

ORD record
ord-f3cc13f4e8a947e0bde26ffff6afca73
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

Loading…