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Triphenylphosphine → HCID 11816425, 화합물

HRID 1797102
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HRID 1797102 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][N:22]=1.C([Sn](CCCC)(CCCC)[CH:35]=[CH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)CCC>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:35](/[C:21]1[N:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)=[CH:36]\[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 783082-Chloro-5-nitropyridineHCID 4372073HCID 4372073, 화합물

생성물 1

HCID 11816425HCID 11816425, 화합물수율 23%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide
용매

실험 절차

Under inert atmosphere (Ar) a mixture of palladium(II)-acetate (0.45 g, 2 mmol) and triphenylphosphine (0.95 g, 3.6 mmol) in DMF (50 ml) was stirred for 0.5 hr at rt. Then 2-chloro-5-nitropyridine (3.2 g, 20 mmol) and tributyl-styryl-stannane (15.7 g, 40 mmol) was added and the mixture was stirred at 130° C. for 15 hr. The solvent was evaporated and the residue partitioned between AcOEt and 1N HCl. The aqueous phase was neutralized with 6N NaOH and extracted with AcOEt. The organic phase was dried with Na2SO4, concentrated and chromatographed (SiO2 with CH2Cl2/CH3OH=97/3) to give the title compound (0.90 g, 23%) as a yellow solid. Mp. 159–160° C. (AcOEt), MS: 196 (M+).

후처리

  1. stirringthe mixture was stirred at 130° C. for 15 hr
  2. customThe solvent was evaporated
  3. customthe residue partitioned between AcOEt and 1N HCl
  4. extractionextracted with AcOEt
  5. dry with materialThe organic phase was dried with Na2SO4
  6. concentrationconcentrated
  7. customchromatographed (SiO2 with CH2Cl2/CH3OH=97/3)

출처 및 근거

ORD 기록
ord-77604f352bed437088fb9c2d79c90ed1
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07034044B2

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