2,4,6-Trimethylbenzeneboronic acid → 1-(6-Mesitylpyridin-2-yl)pentan-2-ol

HRID 598109Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([CH2:8][CH:9]([OH:13])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=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:15]1([CH3:14])[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[C:2]1[N:7]=[C:6]([CH2:8][CH:9]([OH:13])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1-(6-Bromopyridin-2-yl)pentan-2-ol (3.23 g, 13.2 mmol) was dissolved in 30 mL of 1,2-dimethoxyethane. Tetrakis(triphenylphosphine)palladium(0) (0.76 g, 0.66 mmol) was added and the solution was heated to 50° C. for 15 min. After cooling the solution, 2,4,6-trimethylbenzeneboronic acid (2.60 g, 15.9 mmol) in 15 mL 1,2-dimethoxyethane was added to parent solution. Potassium t-butoxide (2.96 g, 26.5 mmol) in 15 mL t-butanol was added last. The reaction was heated at 90° C. for 0.5 h. After cooling, the solution was filtered and concentrated. Flash chromatography (20% ethyl acetate/hexanes) gave the title compound (2.91 g, 77% yield).

Workup

additionwas added to parent solution
temperatureThe reaction was heated at 90° C. for 0.5 h
temperatureAfter cooling
filtrationthe solution was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-5d6f6713b4d14f439713ab545a3ff287
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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