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

HRID 1851162노트

반응식

HRID 1851162 반응식
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])=[CH:6][N:5]2[N:16]=[C:17]([CH3:19])[N:18]=[C:4]2[N:3]=1.[CH:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:21].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:15][C:9]1[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=1[C:7]1[C:2]([C:25]2[CH:26]=[CH:27][C:22]([CH:20]=[O:21])=[CH:23][CH:24]=2)=[N:3][C:4]2[N:5]([N:16]=[C:17]([CH3:19])[N:18]=2)[CH:6]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 867030235-Chloro-6-(2,4-difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

생성물 1

HCID 867030514-[6-(2,4-Difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde수율 81%

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 1 g (3.56 mmol) of the 5-chloro-6-(2,4-difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine described in step 3 and 587.6 mg (3.9 mmol) 4-formylphenylboronic acid in 12 mL 1,2-dimethoxyethane are added 131 mg (0.16 mmol) dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) and 6.9 mL of a sodium carbonate solution (10%). The resulting mixture is heated to 90° C. under an inert gas atmosphere for 2 h. 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; the solvent is evaporated and the residue is purified by chromatography on silica gel (dichloromethane/methanol) to yield 1.01 g (77%) 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. customthe solvent is evaporated
  5. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-7a942d27fe7d4ef78d18a285a301eace
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957064B2

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