3-Isopropylbenzeneboronic acid → 5-[3-(Propan-2-yl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 336394

Reaction equation

HRID 336394 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:12][CH:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)[CH3:14]>C(#N)C.C(=O)([O-])[O-].[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][CH:13]([C:15]1[CH:20]=[C:19]([C:2]2[N:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=1)[CH3:14]

Participants

6

Reactant 2

HCID 27734783-Isopropylbenzeneboronic acidHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 445561185-[3-(Propan-2-yl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amineYield 63%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

A biphasic solution of 5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.800 g, 3.76 mmol, 1.00 equiv), 3-(2-propyl)phenyl boronic acid (0.739 g, 4.51 mmol, 1.20 equiv), bis(triphenylphosphine)palladium(II) chloride (0.264 g, 0.376 mmol, 0.100 equiv) in acetonitrile (6 mL) and 1.0M sodium carbonate aqueous solution (6 mL) was heated in the microwave to 160° C. for 2 min. The reaction mixture was partitioned between saturated aqueous sodium chloride solution (10 mL) and ethyl acetate (20 mL). The collected organic was dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (2.5% methanol in dichoromethane) afforded product as a sticky solid (567 mg, 63%). 1H NMR (500 MHz, CDCl3), δ: 7.74 (m, 1H), 7.68 (m, 1H), 7.36-7.48 (m, 4H), 6.79 (dd, J=7.2, 1.3 Hz, 1H), 4.46 (br s, 2H), 3.01 (m, 1H), 1.31 (d, J=6.9 Hz, 6H).

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium chloride solution (10 mL) and ethyl acetate (20 mL)
  2. dry with materialThe collected organic was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (2.5% methanol in dichoromethane)

Sources & evidence

ORD record
ord-e96686d22c2c4268878fffee847229b6
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Linked notes

Loading…