Potassium Carbonate → HCID 57839072, 화합물

HRID 732955

반응식

HRID 732955 반응식
Cl[C:2]1[C:7]([CH:8]=[O:9])=C[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[C:20]([CH3:23])=[CH:21][CH:22]=1.[C:27]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:7]([CH:8]=[O:9])=[CH:2][N:3]=[C:4]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:5]=2)=[C:19]([CH3:27])[CH:18]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2773336(5-Chloro-2-methylphenyl)boronic acidHCID 57839061HCID 57839061, 화합물

생성물 1

HCID 57839072HCID 57839072, 화합물수율 88.7%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

To a stirred solution of 4-chloro-2-phenylpyrimidine-5-carbaldehyde (50 mg, 0.23 mmol) and 4-chloro-o-toluene boronic acid (48 mg, 0.29 mmol) in dioxane (1 mL) and H2O (0.5 mL) was added Pd(PPh3)4 (26.5 mg, 0.02 mmol), K2CO3 (126.5 mg, 0.92 mmol). The reaction was heated to 85° C. for 6 hrs. After concentration under reduced pressure, the residue was diluted with EtOAc (10 mL) and the organic layer was washed with saturated NH4Cl solution (10 mL), and brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give the crude product (70 mg). The crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane) to give 4-(4-chloro-2-methylphenyl)-2-phenylpyrimidine-5-carbaldehyde (63 mg, 75%) as a white solid.

후처리

  1. concentrationAfter concentration under reduced pressure
  2. additionthe residue was diluted with EtOAc (10 mL)
  3. washthe organic layer was washed with saturated NH4Cl solution (10 mL), and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product (70 mg)
  8. customThe crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-d8a06cc992f54305bf7417ba9ab58325
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589088B2

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