Potassium Carbonate → (4'-Cyano-biphenyl-3-yl)-carbamic acid tert-butyl ester

HRID 1665728노트

반응식

HRID 1665728 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[C:12]([O:16][C:17](=[O:26])[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](Br)[CH:20]=1)([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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:12]([O:16][C:17](=[O:26])[NH:18][C:19]1[CH:24]=[C:23]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:22]=[CH:21][CH:20]=1)([CH3:15])([CH3:13])[CH3:14]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 2757254N-(tert-Butoxycarbonyl)-3-bromoaniline

생성물 1

HCID 67120680(4'-Cyano-biphenyl-3-yl)-carbamic acid tert-butyl ester수율 59%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21962138N,N-Dimethylformamide--water (1/1)용매

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온도
80 °C

실험 절차

A mixture of 4-cyanobenzeneboronic acid (14.7 g, 0.10 mol), 3-bromo-phenyl-carbamic acid tert-butyl ester (27.2 g, 0.10 mol), Pd(Ph3P)4 (11.6 g, 0.01 mol) and K2CO3 (21 g, 0.15 mol) in DMF/H2O (1:1, 350 mL) was stirred under argon at 80° C. overnight. The DMF was evaporated under reduced pressure, and the residue was dissolved in EtOAc (200 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated to dryness. The residue was purified by column chromatography (petroleum ether/EtOAc 50:1) on silica gel to give (4′-cyano-biphenyl-3-yl)-carbamic acid tert-butyl ester (17 g, 59%). 1H NMR (300 MHz, DMSO-d6) δ 9.48 (s, 1 H), 7.91 (d, J=8.4 Hz, 2 H), 7.85 (s, 1 H), 7.76 (d, J=8.4 Hz, 2 H), 7.32-7.48 (m, 3 H), 1.47 (s, 9 H).

후처리

  1. customThe DMF was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc (200 mL)
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography (petroleum ether/EtOAc 50:1) on silica gel

출처 및 근거

ORD 기록
ord-394f163cd7c24dc4b02849d8554a856f
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039491B2

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