Water → [4-(3-Hydroxymethyl-Phenyl)-8-Trifluoromethyl-Quinolin-3-yl]-Phenyl-Methanone

HRID 2104517Notes

Reaction equation

HRID 2104517 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][CH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:31][CH2:32][C:33]1[CH:38]=[C:37]([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:18])([F:20])[F:19])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[C:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:28])[CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 160903243-Benzoyl-8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate

Product 1

HCID 66913719[4-(3-Hydroxymethyl-Phenyl)-8-Trifluoromethyl-Quinolin-3-yl]-Phenyl-MethanoneYield 96%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of (3-benzoyl-8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate). (3.0 g, 6.0 mmol), 3-hydroxymethylphenylboronic acid (1.5 g, 10 mmol), K3PO4 (3.0 g) and Pd(PPh3)4 (0.30 g) in dioxane (30 ml) was heated to reflux. After 3 hr, the reaction was cooled and poured into water. The aqueous layer was extracted with EtOAc, dried, concentrated to give an oil which was purified by column chromatography (eluent 30% EtOAc/Hexane) to give the title compound as a foam (2.6 g, 96%); MS (ESI) m/z 407([M+H]+); 1H NMR (DMSO) δ 9.149 (s, 1H), 8.33 (d, 1H, J=7.1 Hz), 7.96 (d, 1H), 7.8 Hz), 7.80 (t, 1H, J=7.4 Hz), 7.62 (d, 2H, H=7.1 Hz), 7.55 (t, 1H, J=7.5 Hz), 7.40-7.28 (m, 5H), 7.18-7.14 (m, 1H), 5.23 (t, 1H, J=5.6 Hz), 4.41 (d, 1H, J=5.6 Hz).

Workup

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customdried
  4. concentrationconcentrated
  5. customto give an oil which
  6. customwas purified by column chromatography (eluent 30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-9b8724f09ffc46c0a0daf7ef3782edf9
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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