Sodium Carbonate → HCID 67980833, compound

HRID 2406986Notes

Reaction equation

HRID 2406986 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[CH:22]=[CH:21][C:20]([CH:23]([OH:27])[CH2:24][CH2:25][CH3:26])=[CH:19][C:16]=1[C:17]#[N:18].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[OH:27][CH:23]([C:20]1[CH:19]=[C:16]([C:17]#[N:18])[C:15]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)=[CH:22][CH:21]=1)[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 67980648HCID 67980648, compound

Product 1

HCID 67980833HCID 67980833, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

A sealed flask was charged with the (4-(trifluoromethyl)phenyl)boronic acid (1.09 g, 5.76 mmol), 2-bromo-5-(1-hydroxybutyl)benzonitrile (1.33 g, 5.23 mmol) and acetonitrile (17 mL). Once everything get into solution, 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (115 mg, 157 μmol) was added followed by the sodium carbonate 2M aq. (6.54 mL, 13.1 mmol). Flask sealed and heated at 140° C. for 1 hour. Organic solvent removed under reduced pressure and ethyl acetate added. Organics washed with water (1×), with brine (1×), dried over sodium sulfate, filtered and concentrated to provide the crude material. Purification by silica gel flash chromatography (Ethyl Acetate/Heptane) provide the title compound as a colorless oil (1.39 g, 83.2%). 1H NMR (400 MHz, DMSO-d6) δ 0.87-0.93 (m, 3 H) 1.25-1.45 (m, 2 H) 1.57-1.67 (m, 2 H) 4.64-4.70 (m, 1 H) 5.41 (d, J=4.68 Hz, 1 H) 7.64 (d, J=8.00 Hz, 1 H) 7.75-7.79 (m, 1 H) 7.82 (d, J=8.00 Hz, 2 H) 7.88-7.94 (m, 3 H).

Workup

  1. customOnce everything get into solution, 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (115 mg, 157 μmol)
  2. additionwas added
  3. customFlask sealed
  4. customOrganic solvent removed under reduced pressure and ethyl acetate
  5. additionadded
  6. washOrganics washed with water (1×), with brine (1×)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto provide the crude material
  11. customPurification by silica gel flash chromatography (Ethyl Acetate/Heptane)

Sources & evidence

ORD record
ord-0dc0f31cb2334ba29b641c499d71bbe4
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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