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Potassium Phosphate, Tribasic → 2-Fluoro-3-[4-methyl-2-(morpholin-4-yl)pyrimidin-5-yl]benzaldehyde

HRID 2171672
ノート
印刷プレビュー

反応式

HRID 2171672 の反応式
Br[C:2]1[C:3]([CH3:14])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[F:15][C:16]1[C:21]([CH:22]=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[F:15][C:16]1[C:17]([C:2]2[C:3]([CH3:14])=[N:4][C:5]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:18][CH:19]=[CH:20][C:21]=1[CH:22]=[O:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 62657Potassium Phosphate, Tribasic2 回HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl2 回HCID 162178292-Fluoro-3-formylphenylboronic Acid (contains varying amounts of Anhydride)2 回HCID 683089314-(5-Bromo-4-methylpyrimidin-2-yl)morpholine

生成物 1

HCID 866862302-Fluoro-3-[4-methyl-2-(morpholin-4-yl)pyrimidin-5-yl]benzaldehyde
収率 64.9%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒2 回HCID 962Water溶媒3 回HCID 1140Toluene溶媒HCID 6212Chloroform溶媒

反応条件

温度
100 °C

実験手順

4-(5-Bromo-4-methylpyrimidin-2-yl)morpholine (372 mg), (2-fluoro-3-formylphenyl)boronic acid (315 mg), and potassium phosphate (918 mg) were mixed with toluene (10 ml) and water (10 ml), and palladium acetate (16 mg) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (59 mg) were added thereto, followed by stirring at 100° C. for 4 hours. (2-Fluoro-3-formylphenyl)boronic acid (315 mg), potassium phosphate (918 mg), palladium acetate (16 mg), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (59 mg), and water (1 ml) were added to the reaction mixture, followed by stirring at 100° C. overnight. The reaction mixture was cooled to room temperature, CHCl3 and water were then added thereto, and the insoluble matter was removed by filtration. The organic layer of the filtrate was washed with water and saturated brine, dried over Na2SO4, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane/CHCl3) to obtain 2-fluoro-3-[4-methyl-2-(morpholin-4-yl)pyrimidin-5-yl]benzaldehyde (282 mg).

後処理

  1. additionwere added
  2. stirringby stirring at 100° C. overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe insoluble matter was removed by filtration
  5. washThe organic layer of the filtrate was washed with water and saturated brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane/CHCl3)

出典と根拠

ORDレコード
ord-d8347a9324814cacaa8031d091228b94
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09051283B2

反応ノート

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