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

HRID 336394

反応式

HRID 336394 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒HCID 10340Sodium Carbonate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e96686d22c2c4268878fffee847229b6
出典データセット
uspto-grants-2014_11
特許番号
US08889673B2

関連ノート

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