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

HRID 250950

반응식

HRID 250950 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 772302663-p-Tolyl-pyridine-2-carbaldehyde수율 77%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 22732251Tetrahydrofuran dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4c5c936c45ed40f7af64fc58220f4daf
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863293B2

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