Potassium Carbonate → HCID 10286020, compound

HRID 2099502Notes

Reaction equation

HRID 2099502 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=1.[Cl:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.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>[Cl:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:3]=[N:4][N:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)[CH:6]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 113451062-(4-bromo-1h-pyrazol-1-yl)pyridine

Product 1

HCID 10286020HCID 10286020, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
70 °C

Procedure

A solution of 2-(4-bromo-1H-pyrazol-1-yl)pyridine (0.669 g, 3 mmol), 3-chlorophenylboronic acid (0.468 g, 3 mmol) and potassium carbonate (0.828 g, 6 mmol) in a mixture of ethyleneglycol dimethyl ether (20 mL) and H2O (4 mL) were degassed by argon bubbling for 15 min., then tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) was added and degasing continued a further 15 min. The solution was stirred at 70° C. for 14 h, whereupon H2O (30 mL) was added, then extracted with EtOAc (3×30 mL) and the combined extracts washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo and the crude residue was chromatographed on silica gel eluting with EtOAc:hexane (1:4) to afford a white solid which was recrystallized from EtOAc/Hexane to give 2-[4(3-chlorophenyl)-1H-pyrazol-1-yl]pyridine. MP=110-111° C. 1H NMR (CD3Cl, 300 MHz) δ 8.83 (d, 1H), 8.42 (dd, 1H), 7.99 (s, 1H), 7.99 (d, 1H), 7.82 (ddd, 1H), 7.57 (t, 1H), 7.45 (dt, 1H), 7.32 (t, 1H), 7.25˜7.18 (m, 2H). MS (ESI) 255.9 (M++H).

Workup

  1. customwere degassed by argon bubbling for 15 min.
  2. customdegasing
  3. additionwas added
  4. extractionextracted with EtOAc (3×30 mL)
  5. washthe combined extracts washed with brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customthe crude residue was chromatographed on silica gel eluting with EtOAc:hexane (1:4)
  9. customto afford a white solid which
  10. customwas recrystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-ae1d7f89507c4508b6e5083c2c2ba2c0
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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