tert-Butyl piperazine-1-carboxylate → HCID 67094789, 화합물

HRID 1710600

반응식

HRID 1710600 반응식
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Br[C:48]1[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=1[O:57][C:58]([F:61])([F:60])[F:59].[C:62]([O:66][C:67]([N:69]1[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]1)=[O:68])([CH3:65])([CH3:64])[CH3:63].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:62]([O:66][C:67]([N:69]1[CH2:74][CH2:73][N:72]([C:48]2[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=2[O:57][C:58]([F:61])([F:60])[F:59])[CH2:71][CH2:70]1)=[O:68])([CH3:65])([CH3:63])[CH3:64]

참가 물질

7

반응물 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 247216412-Bromo-4-nitro(trifluoromethoxy)benzene

생성물 1

HCID 67094789HCID 67094789, 화합물수율 59.2%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매2회

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온도
60 °C

실험 절차

A mixture of 0.048 g palladium(II)-acetate (0.214 mmol) and 0.133 g BINAP (0.214 mmol) in 7 mL toluene was heated to 60° C., stirred for 10 min. and the obtained suspension was added dropwise to a solution of 0.51 g 2-bromo-4-nitro-1-(trifluoromethoxy)benzene (1.783 mmol), 0.343 g tert.butyl-piperazine-1-carboxylate (1.842 mmol) and 0.232 g sodium tert-butoxide (2.414 mmol) in 8 mL of toluene. The thus obtained reaction mixture was treated at 130° C. for 1.5 h in a commercial microwave oven. The organic layer was washed with water, the aqueous phase was extracted with dichloromethane and the combined organic layers were extracted with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was further purified via silica gel chromatography using a ISCO Companion system (eluent cyclohexane-ethyl acetate 5-25%) to yield 0.413 g of product.

후처리

  1. customThe thus obtained reaction mixture
  2. additionwas treated at 130° C. for 1.5 h in a commercial microwave oven
  3. washThe organic layer was washed with water
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. extractionthe combined organic layers were extracted with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe crude product was further purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-33e18adf3c554e2bb7578855c5491576
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790727B2

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