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

HRID 2171672
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HRID 2171672 반응식
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]
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참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, Tribasic2회HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl2회HCID 162178292-Fluoro-3-formylphenylboronic Acid (contains varying amounts of Anhydride)2회HCID 683089314-(5-Bromo-4-methylpyrimidin-2-yl)morpholine

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매2회HCID 962Water용매3회HCID 1140Toluene용매HCID 6212Chloroform용매

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d8347a9324814cacaa8031d091228b94
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051283B2

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