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Sodium Carbonate → 4-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

HRID 1851191
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인쇄 미리보기

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HRID 1851191 반응식
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:14]=[CH:15][CH:16]=[C:4]2[N:3]=1.[CH:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.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]>[C:8]1([C:7]2[C:2]([C:22]3[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=3)=[N:3][C:4]3[N:5]([N:14]=[CH:15][CH:16]=3)[CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 866306645-Chloro-6-phenylpyrazolo[1,5-a]pyrimidine

생성물 1

HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

시약·촉매·용매 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매
HCID 962
Water
용매
HCID 6344Dichloromethane용매
HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

To a mixture of 300 mg of the mixture from step 3 and 360 mg 4-formylphenylboronic acid in 9 mL 1,2-dimethoxyethane were added 1.8 mL of a 10% w/w sodium carbonate solution and 36 mg dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) and the resulting mixture was heated to 80° C. under an inert gas atmosphere for 18 h. The work up was performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers were dried over sodium sulphate, evaporated and the residue was purified by chromatography on silica gel (dichloromethane/methanol). The product was crystallized from ethyl acetate.

후처리

  1. customseparating
  2. extractionthe phases and extraction of the aqueous phase with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. customevaporated
  5. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol)
  6. customThe product was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-9e342c6e86044594902db3f21420271c
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957064B2

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