2,4,6-Trimethylbenzeneboronic acid → HCID 67267450, compound

HRID 598115Notes

Reaction equation

HRID 598115 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1B(O)O.CC(C)([O-])C.[K+]>COCCOC.C(O)(C)(C)C.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>[C:11]1([CH3:10])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 3517811(6-Bromopyridin-2-yl)methanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 67267450HCID 67267450, compoundYield 68.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6386tert-ButanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

(6-Bromopyridin-2-yl)-methanol (4.23 g, 22.5 mmol) was dissolved in 1,2-dimethoxyethane. Tetrakis(triphenylphosphine)palladium(0) (1.30 g, 1.12 mmol) was added and the reaction stirred for 15 minutes at 50° C. Upon cooling, 2,4,6-trimethylbenzeneboronic acid (3.69 g, 22.5 mmol) in 20 mL 1,2-dimethoxyethane was added to the reaction followed by potassium t-butoxide (5.05 g, 50.0 mmol) in 20 mL of t-butanol. The reaction was heated at 90° C. for 0.5 hr. The solution was cooled and filtered through paper. Flash chromatography (30% ethyl acetate/hexanes) gave the desired product as a white solid (3.50 g, 68% yield).

Workup

  1. temperatureUpon cooling
  2. temperatureThe reaction was heated at 90° C. for 0.5 hr
  3. temperatureThe solution was cooled
  4. filtrationfiltered through paper

Sources & evidence

ORD record
ord-77d2ea182390430188291901030b97bd
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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