Sodium Carbonate → 3-p-Tolyl-pyridine-2-carbaldehyde

HRID 250950

反応式

HRID 250950 の反応式
Br[C:2]1[C:3]([CH:8]=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1COCC1.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:11]1([CH3:10])[CH:16]=[CH:15][C:14]([C:2]2[C:3]([CH:8]=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:12]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 164142313-Bromopyridine-2-carbaldehyde

生成物 1

HCID 772302663-p-Tolyl-pyridine-2-carbaldehyde収率 77%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 22732251Tetrahydrofuran dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

To a stirred degassed solution of 3-bromo-2-pyridinecarboxaldehyde (198 mg, 1.06 mmol) and 4-methylbenzene boronic acid (152 mg, 1.12 mmol) in DME/THF (3.5 mL, 2.5:1) were added a 2 M Na2CO3 solution (0.9 mL) and Pd(PPh3)4 (63 mg, 0.055 mmol). The reaction mixture was flushed with Ar and maintained under Ar while being heated at 90° C. overnight. The mixture was then cooled and diluted with EtOAc (40 mL) and brine (30 mL). The organic layer was washed with brine (1×30 mL), dried (Na2SO4), filtered and concentrated. Purification of the resultant oil by column chromatography with silica gel (Hexanes/EtOAc, 2:1) afforded 3-p-tolyl-pyridine-2-carbaldehyde (161 mg, 77%) as a yellow oil. 1H NMR (CDCl3) δ 2.43 (s, 3H), 7.25-7.28 (m, 4H), 7.53 (dd, 1H, J=9, 6 Hz), 7.79 (dd, 1H, J=9, 1 Hz), 8.80 (dd, J=3, 1 Hz), 10.09 (s, 1H).

後処理

  1. customThe reaction mixture was flushed with Ar
  2. temperaturemaintained under Ar
  3. temperatureThe mixture was then cooled
  4. additiondiluted with EtOAc (40 mL) and brine (30 mL)
  5. washThe organic layer was washed with brine (1×30 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the resultant oil by column chromatography with silica gel (Hexanes/EtOAc, 2:1)

出典と根拠

ORDレコード
ord-4c5c936c45ed40f7af64fc58220f4daf
出典データセット
uspto-grants-2011_01
特許番号
US07863293B2

関連ノート

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