2,4,6-Trimethylbenzeneboronic acid → HCID 67266808, compound

HRID 598096Notes

Reaction equation

HRID 598096 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1.[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1B(O)O.CC(C)([O-])C.[K+]>COCCOC.CC(O)(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:17]1([CH3:16])[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[C:2]1[N:7]=[C:6]([CH2:8][N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 23665647Potassium tert-butoxideHCID 86613887HCID 86613887, compound

Product 1

HCID 67266808HCID 67266808, compoundYield 48%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
50 °C

Procedure

N-[(6-Bromopyridin-2-yl)methyl]-N-propylpropan-1-amine (7.0 g, 26 mmol) was dissolved in 1,2-dimethoxyethane (100 mL). Tetrakis(triphenylphosphine)palladium(0) (1.49 g, 1.29 mmol) was added and the solution was heated to 50° C. for 15 minutes. The solution was cooled and 2,4,6-trimethylbenzeneboronic acid (4.44 g, 27.1 mmol) in 30 mL 1,2 dimethoxyethane was added followed by potassium tert-butoxide (5.79 g, 51.6 mmol) in 30 mL of tBuOH. The reaction was heated at 90° C. for 0.5 h. The solution was filtered through filter paper and concentrated. Flash chromatography gave 3.83 g of the title compound (48% yield).

Workup

  1. temperatureThe solution was cooled
  2. temperatureThe reaction was heated at 90° C. for 0.5 h
  3. filtrationThe solution was filtered
  4. filtrationthrough filter paper
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b7cc21dd0e924abfb0083ab481dedb39
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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