Water → 4-(2-Benzofuranyl)-2,8-bis(trifluoromethyl)quinoline

HRID 1370342Notes

Reaction equation

HRID 1370342 reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.[O:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH:22]=[C:21]1B(O)O.C([O-])([O-])=O.[Na+].[Na+].O>C(COC)OC.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:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH:22]=[C:21]1[C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 40712424-Bromo-2,8-bis(trifluoromethyl)quinoline

Product 1

HCID 185114194-(2-Benzofuranyl)-2,8-bis(trifluoromethyl)quinolineYield 64%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 4-bromo-2,8-bis(trifluoromethyl)quinoline (500 mg, 1.45 mmol) in dry dimethoxyethane (10 mL) was treated with tetrakis(triphenylphosphine)palladium (2.3 mg, 10 mol %), stirred for 10 min, treated with benzofuran-2-boronic acid (235 mg, 1.45 mmol) and 2-M Na2CO3 solution (1.45 mL, 2.9 mmol) then refluxed for 2 h. The mixture was cooled, treated with water (10 mL), extracted with EtOAc (3×20 mL), the organic phase was washed with brine (20 mL), dried (MgSO4), concentrated in vacuo and the resulting yellow solid recrystallised from heptane to give the title compound (351 mg, 64%) as an off-white crystalline solid: mp 129-130° C.; IR νmax (Nujol)/cm−1 2924, 1592, 1463, 1314, 1145, 1116, 1010, 749 and 691; NMR δH (400 MHz, CDCl3) 7.35 (1H, t, J 7.1 Hz), 7.42-7.47 (2H, m), 7.65 (1H, d, J 7.5 Hz), 7.73 (1H, d, J 8.0 Hz), 7.80 (1H, t, J 7.9 Hz), 8.19-8.23 (2H, m) and 8.86 (1H, d, J 9.0 Hz).

Workup

  1. temperaturethen refluxed for 2 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with EtOAc (3×20 mL)
  4. washthe organic phase was washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe resulting yellow solid recrystallised from heptane

Sources & evidence

ORD record
ord-ce3dcb122d18436698977a0022023724
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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