Water → HCID 11564945, compound

HRID 985503Notes

Reaction equation

HRID 985503 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.O>COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2734370(3-Methoxyphenyl)boronic acidHCID 167404763-Bromo-7-methylimidazo[1,2-a]pyridine

Product 1

HCID 11564945HCID 11564945, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 3-bromo-7-methylimidazo[1,2-α]pyridine (18.0 g, 86 mmol) and 3-methoxyphenylboronic acid (17.0 g, 112 mmol) in 1,2-dimethoxyethane (250 ml) and sodium carbonate (120 ml of a 2M aqueous solution) was degassed for 25 minutes. Tetrakis(triphenylphosphine)pallidum(0) (500 mg, 0.4 mmol) was then added and the mixture heated at reflux for 17 hours. After cooling to ambient temperature the reaction was poured into water (400 ml), extracted with ethyl acetate (3×400 ml) and the combined organics dried over anhydrous magnesium sulphate. Filtration and evaporation to dryness afforded 3-(3-methoxyphenyl)-7-methylimidazo[1,2-α]pyridine as a colourless oil (19 g, 93%). 1H NMR (360 MHz, CDC3) δH 2.40 (3H, s), 3.84 (3H, s), 6.63-6.65 (1H, m), 6.91-6.95 (1H, m), 7.05-7.07 (1H, m), 7.10-7.12 (1H, m), 7.30-7.38 (1H, m), 7.42 (1H, s), 7.66 (1H, s), 8.22 (1H, d, J 7); m/z (ES+) 239 (M++H).

Workup

  1. customwas degassed for 25 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux for 17 hours
  4. extractionextracted with ethyl acetate (3×400 ml)
  5. dry with materialthe combined organics dried over anhydrous magnesium sulphate
  6. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-dc8fea058bcd46fbb4ef20aa47fb163b
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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