Dimethylformamide → Tert-butyl [2-(3-cyanophenyl)ethyl]carbamate

HRID 2239584노트

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HRID 2239584 반응식
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1.[CH3:18][N:19](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1)#[N:19]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 18315328Tert-butyl 3-bromophenethylcarbamate

생성물 1

HCID 86617889Tert-butyl [2-(3-cyanophenyl)ethyl]carbamate수율 64.3%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

tert-Butyl [2-(3-bromophenyl)ethyl]carbamate (0.60 g, 1.99 mmol) was dissolved in dry DMF (18 mL) in a under nitrogen atmosphere. Zinc cyanide (0.47 g, 3.99 mmol) and tetrakis(triphenylphosphine)palladium (0.18 g, 0.16 mmol) was added. The reaction mixture was heated in a microwave reactor at 150° C. for 20 mins. The procedure was repeated two more times with equal amount of starting material and the resulting three mixtures were combined and diluted with EtOAc. The mixture was washed with saturated aqueous NaHCO3 and water, dried with Na2SO4, filtered and evaporated. The crude product was purified using Biotage Horizon HPFC system using Heptane and EtOAc as eluant affording the title compound (0.95 g, 64.3%). 1H NMR (500 MHz, CDCl3): δ 1.39 (s, 9H), 2.82 (t, 2H), 3.34 (q, 2H), 4.75 (bs, 1H), 7.37-7.50 (m, 4H); 13C NMR (125 MHz, CDCl3): δ 28.57, 36.09, 41.63, 79.61, 112.69, 119.05, 129.56, 130.38, 132.57, 133.68, 140.86, 156.06.

후처리

  1. washThe mixture was washed with saturated aqueous NaHCO3 and water
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified

출처 및 근거

ORD 기록
ord-12c919e0d743408d8e2aa1905bc665c2
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723333B2

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