Potassium Carbonate → 5-Methyl-2-phenylpyridine

HRID 736379

反応式

HRID 736379 の反応式
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+]>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.CC#N>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:12][CH:13]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 5642162-Bromo-5-methylpyridine

生成物 1

HCID 474675-Methyl-2-phenylpyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

Phenylboronic acid (732 mg, 6 mmol), 2-bromo-5-methylpyridine (1.03 g, 5.99 mmol), and Pd (PPh3)4 (350 mg, 0.303 mmol) were heated in 0.4 M K2CO3 (30 mL, 12 mmol) and CH3CN (30 mL) at 90° overnight. The mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between brine and ethyl acetate. The organic layer was separated, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (9:1 hexanes:ethyl acetate) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.50 (m, 1H), 8.05 (m, 2H), 7.85 (d, J=8.4 Hz, 1H), 7.68-7.71 (m, 1H), 7.37-7.50 (m, 3H), 2.34 (s, 3H); MS (APCI+) m/z 170 (M+H)+.

後処理

  1. customat 90°
  2. customovernight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between brine and ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (9:1 hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-9e7489330df747f0a94e6c7b2828f6bb
出典データセット
uspto-grants-2009_09
特許番号
US07595332B2

関連ノート

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