Water → 4-(Pyridazin-4-yl)benzyl alcohol

HRID 2359829Notes

Reaction equation

HRID 2359829 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[N:4][CH:3]=1.[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.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:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=2)=[CH:3][N:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 178889274-Bromopyridazine

Product 1

HCID 667174174-(Pyridazin-4-yl)benzyl alcoholYield 64%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-bromopyridazine (131 mg, 0.824 mmol) in 1,2-dimethoxyethane (16.4 ml) were added 4-hydroxymethylphenylboronic acid (189 mg, 1.24 mmol), potassium carbonate (517 mg, 3.74 mmol) and water (8.2 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (73.5 mg, 0.0636 mmol) was then added, followed by heating to reflux for 5 hours under argon atmosphere. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The resulting residue was subjected to reversed phase column chromatography (column; Megabond Elut™ C18 (manufactured by Varian, Inc.), eluent; acetonitrile:water=0:1→1:4 (V/V), then methanol), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (97.7 mg) as a slightly brown solid. (Yield: 64%)

Workup

  1. temperatureby heating
  2. temperatureto reflux for 5 hours under argon atmosphere
  3. customAfter completion of the reaction
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. additionacetonitrile:water=0:1→1:4 (V/V), then methanol), and fractions containing the desired compound
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc50e680d593460b83d9d0ba366c7189
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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