Tetrahydrofuran → HCID 60209896, compound

HRID 1042630Notes

Reaction equation

HRID 1042630 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1COCC1.Cl[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][N:16]=1.[CH3:23][N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:23][N:24]1[CH:28]=[C:27]([C:15]2[N:16]=[CH:17][C:18]([CH2:21][OH:22])=[CH:19][CH:20]=2)[CH:26]=[N:25]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 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 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a pressure vessel was charged Pd(dppf)Cl2 (CH2Cl2 adduct, 341 mg, 0.418 mmol) and potassium phosphate (1.48 g, 6.97 mmol). Nitrogen was blown over the solids and THF (8 mL) and H2O (1.6 mL) were added. A solution of 2-chloro-5-hydroxymethylpyridine (500 mg, 3.48 mmol) and 1-methylpyrazole-4-boronic acid pinacol ester (797 mg, 3.83 mmol) was added; the resulting solution was capped and heated at 80° C. overnight, then cooled to rt and diluted with ethyl acetate. The organic solution was washed 1× with saturated aqueous sodium bicarbonate and 1× with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 30-100% ethyl acetate in hexanes to provide [6-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]methanol that gave a mass ion (ES+) of 190.1 for [M+H]+.

Workup

  1. additionwere added
  2. customthe resulting solution was capped
  3. temperaturecooled to rt
  4. washThe organic solution was washed 1× with saturated aqueous sodium bicarbonate and 1× with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via silica gel chromatography
  9. washeluting with 30-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-556e321bb714400cb5b46a3612a41639
Source dataset
uspto-grants-2013_10
Patent number
US08557992B2

Reaction notes

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