Potassium Carbonate → HCID 10236192, compound

HRID 2099508Notes

Reaction equation

HRID 2099508 reaction equation
FC(F)(F)S(O[C:7]1[CH:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:8]=1)(=O)=O.F[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.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>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:9]1[CH:10]=[CH:11][C:7]([C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[C:24]#[N:25])=[N:8]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 678803-FluorobenzonitrileHCID 111971281-pyridin-2-yl-1H-pyrazol-3-yl trifluoromethanesulfonate

Product 1

HCID 10236192HCID 10236192, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
65 °C

Procedure

1-Pyridin-2-yl-1H-pyrazol-3-yl trifluoromethanesulfonate (0.211 g, 0.72 mmol), 3-fluorobenzonitrile (0.111 g, 0.76 mmol) and potassium carbonate (0.209 g, 1.51 mmol) in a mixture of ethyleneglycol dimethyl ether (20 mL) and water (4 mL) was degassed by argon bubbling for 15 min., then tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) was added the resulting solution degassed for a further 15 min. The solution was stirred at 65° C. for 12 h. The reaction mixture was quenched with water (30 mL), then extracted with EtOAc (3×30 mL) and washed with brine. The combined organic phase was dried over Na2SO4 and concentrated in vacuo. The crude residue was chromagraphed on silica gel eluting with EtOAc:hexane (2:3) to afford a white solid which was recrystallized from EtOAc-hexane to give 3-(1-pyridin-2-yl-1H-pyrazol-3-yl)benzonitrile as a white solid. 1H NMR (CD3Cl, 300 MHz) δ 8.64 (d, 1H), 8.44 (d, 1H), 8.25 (s, 1H), 8.14 (d, 1H), 8.10 (d, 1H), 7.87 (t, 1H), 7.64 (d, 1H), 7.55 (t, 1H), 7.24 (dd, 1H), 6.80 (d, 1H). MS (ESI) 247 (M++H).

Workup

  1. customwas degassed by argon bubbling for 15 min.
  2. customdegassed for a further 15 min
  3. customThe reaction mixture was quenched with water (30 mL)
  4. extractionextracted with EtOAc (3×30 mL)
  5. washwashed with brine
  6. dry with materialThe combined organic phase was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto afford a white solid which
  9. customwas recrystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-f80eb8e7957b4bf6aa1cdf4ea68b9798
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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