Potassium Phosphate, Tribasic → HCID 60209896, compound

HRID 1497320Notes

Reaction equation

HRID 1497320 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:13]=[N:12]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:10][N:11]1[CH:15]=[C:14]([C:2]2[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=2)[CH:13]=[N:12]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 177161(6-Chloropyridin-3-yl)methanolHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 60209896HCID 60209896, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

In a microwave vial containing (6-chloropyridin-3-yl)methanol (H1) (0.25 g, 1.7 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole (63 mg, 0.30 mmol), Pd2(dba)3 (16 mg, 0.02 mmol), and tricyclohexylphosphine (12 mg, 0.04 mmol) was added 7.0 mL of dioxane and 2.3 mL 1.7 M aqueous tribasic potassium phosphate. The reaction was heated to 140° C. in a microwave reactor for 1.5 h. The reaction mixture was extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 0-15% methanol in methylene chloride to afford [6-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]methanol (H2) that gave a mass ion (ES+) of 190.2 for M+H+.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluting with 0-15% methanol in methylene chloride

Sources & evidence

ORD record
ord-c0f87483b7f1454abaa52cb9ec55b9d9
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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