Sodium Carbonate → 4-[6-(3-Fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde

HRID 1851165노트

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HRID 1851165 반응식
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][N:5]2[N:15]=[C:16]([CH3:18])[N:17]=[C:4]2[N:3]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([C:24]3[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=3)=[N:3][C:4]3[N:5]([N:15]=[C:16]([CH3:18])[N:17]=3)[CH:6]=2)[CH:13]=[CH:12][CH:11]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 867030255-Chloro-6-(3-fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

생성물 1

HCID 867030534-[6-(3-Fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde수율 91.3%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

To a mixture of 0.73 g (2.8 mmol) 5-chloro-6-(3-fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and 458.3 mg (3.1 mmol) 4-formylphenylboronic acid in 14 mL 1,2-dimethoxyethane are added 5.2 mL of a sodium carbonate solution (10%) and 102 mg (0.13 mmol) dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II). The resulting mixture is heated to 90° C. under an inert gas atmosphere over night. The reaction mixture is diluted with water and extracted three times with dichloromethane. The combined organic layers are washed with brine and dried over sodium sulphate. After evaporation of the solvent the residue is purified by chromatography on silica gel (dichloromethane/methanol) to yield 0.85 g (87.3%) of the desired aldehyde.

후처리

  1. extractionextracted three times with dichloromethane
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over sodium sulphate
  4. customAfter evaporation of the solvent the residue
  5. customis purified by chromatography on silica gel (dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-407df0aba34843ff99af2e2d4a3a7710
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957064B2

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