4-Fluorophenylboronic acid → HCID 11740960, compound

HRID 1064266Notes

Reaction equation

HRID 1064266 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:23]#[N:24])[C:5]([C:8]2[CH:13]=[C:12]([C:14]3[N:15]=[C:16](SC)[N:17]=[N:18][CH:19]=3)[CH:11]=[CH:10][C:9]=2[F:22])=[CH:6][CH:7]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>C1COCC1.C(Cl)Cl.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>[F:1][C:2]1[CH:3]=[C:4]([C:23]#[N:24])[C:5]([C:8]2[CH:13]=[C:12]([C:14]3[N:15]=[C:16]([C:29]4[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=4)[N:17]=[N:18][CH:19]=3)[CH:11]=[CH:10][C:9]=2[F:22])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 22273589HCID 22273589, compound

Product 1

HCID 11740960HCID 11740960, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4,2′-difluoro-5′-(3-methylsulfanyl-[1,2,4]triazin-5-yl)biphenyl-2-carbonitrile (0.11 g, 0.32 mmol), cuprous 3-methylsalicylate (0.153 g, 0.711 mmol) and 4-fluorobenzeneboronic acid (0.1 g, 0.711 mmol) in dry THF (8 ml) was added tetrakis(triphenylphosphine)palladium(0) (0.037 g, 0.032 mmol) and the mixture heated at 50° C. for 5 h. The reaction was allowed to cool to ambient temperature, diluted with DCM (20 ml) and filtered through a glass fibre filter. The dark brown solution was evaporated to give a brown solid. The crude product was chromatographed on silica (eluted with 3% MeOH in DCM) to give the product as a yellow solid. Recrystallisation from DCM/MeOH gave the title compound as a pale yellow solid (52 mg): δH (400 MHz, CDCl3) 7.24 (2H, m), 7.44-7.49 (2H, m), 7.55-7.62 (2H, m), 8.36-8.39 (2H, m), 8.64-8.69 (2H, m), 9.62 (1H, s); m/z (ES+) 389 (M++H).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered through a glass fibre filter
  3. customThe dark brown solution was evaporated
  4. customto give a brown solid
  5. customThe crude product was chromatographed on silica (eluted with 3% MeOH in DCM)

Sources & evidence

ORD record
ord-76cb3b1211c1431390284f09c5753936
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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