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Phenylboronic Acid → Benzophenone (6-chloropyrimidin-4-yl)hydrazone

HRID 37885
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인쇄 미리보기

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HRID 37885 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[C:9](=[N:22][NH2:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC(C)([O-])C.[Na+].C1(B(O)O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:23][N:22]=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 66827Phenylboronic AcidHCID 709434,6-DichloropyrimidineHCID 79304DiphenylmethylidenehydrazineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

생성물 1

HCID 86672326Benzophenone (6-chloropyrimidin-4-yl)hydrazone

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

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온도
90 °C

실험 절차

10.0 g (67.1 mmol) of 4,6-dichloropyrimidine, 14.5 g (73.8 mmol) of benzophenone hydrazone, 9.03 g (94.0 mmol) of sodium tert-butoxide, 409 mg (3.36 mmol) of phenylboronic acid, 301 mg (1.34 mmol) of palladium(II) acetate and 384 mg (1.34 mmol) of rac-2,2′-bis-(diphenylphosphino)-1,1′-binaphthalene are combined. The mixture is degassed and vented twice with argon, 400 ml of dry degassed toluene are added, the mixture is again degassed and vented twice with argon and heated at 90° C. overnight. After cooling, the reaction mixture is poured into water, the aqueous phase is extracted with ethyl acetate, the combined organic phases are concentrated and the residue is taken up in a mixture of dichloromethane and diethyl ether. The precipitate that remains is filtered off with suction (and discarded), the filtrate is concentrated and the residue is purified by column chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 8:2).

후처리

  1. customThe mixture is degassed
  2. customof dry
  3. customdegassed toluene
  4. additionare added
  5. customthe mixture is again degassed
  6. temperatureAfter cooling
  7. additionthe reaction mixture is poured into water
  8. extractionthe aqueous phase is extracted with ethyl acetate
  9. concentrationthe combined organic phases are concentrated
  10. additionthe residue is taken up in a mixture of dichloromethane and diethyl ether
  11. filtrationThe precipitate that remains is filtered off with suction (and discarded)
  12. concentrationthe filtrate is concentrated
  13. customthe residue is purified by column chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 8:2)

출처 및 근거

ORD 기록
ord-85eeaee5f22249eba27910310d48eb54
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08524699B2

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