Phenylboronic Acid → HCID 66914131, compound

HRID 2104607Notes

Reaction equation

HRID 2104607 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[C:15]([C:16]=2O)=[CH:14][CH:13]=[CH:12][C:11]=3[C:18]([F:21])([F:20])[F:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=N[C:26]2[C:31](C=1O)=[CH:30][CH:29]=[CH:28][C:27]=2C(F)(F)F.C1(B(O)O)C=CC=CC=1.C([O-])(O)=O.[Na+]>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.O.CO.C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[C:15]([C:16]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[C:18]([F:21])([F:20])[F:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 178515289HCID 178515289, compoundHCID 178515327HCID 178515327, compound

Product 1

HCID 66914131HCID 66914131, compoundYield 59%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3-Phenyl-8-(trifluoromethyl)quinolin-4-ol: A solution of 3-bromo-8-(trifluoromethyl)quinolin-4-ol (3.2 g, 10.95 mmol) and phenyl boronic acid (2.67 g, 21.91 mmol) in 2:1 toluene:methanol (120 mL) and sat aq NaHCO3 (40 mL) is treated with Pd(PPh3)4 (760 mg) and heated at reflux overnight. The reaction is poured into water and extracted with ethyl acetate. The combined extracts are washed with 2N aq NaOH, water, brine, and dried with magnesium sulfate. The extracts are concentrated and the residue is chromatographed with 1:4 ethyl acetate:hexanes to afford the title compound as a yellow solid (6.4 g, 59%). mp 272-275° C.; MS (ESI) m/z 290; MS (ESI) m/z 288; HRMS: calcd for C16H10NF3O+H, 290.07927; found (ESI_FT, [M+H]1+), 290.07816.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts are washed with 2N aq NaOH, water, brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationThe extracts are concentrated
  7. customthe residue is chromatographed with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-30ce3a9722704f9ab6f3e0aa966074c7
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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