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

HRID 1851162ノート

反応式

HRID 1851162 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7a942d27fe7d4ef78d18a285a301eace
出典データセット
uspto-grants-2015_02
特許番号
US08957064B2

反応ノート

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