Dichloromethane → 1,1-Dimethylethyl (2-{[3'-(aminocarbonyl)-2-methyl-4-biphenylyl]oxy}ethyl)carbamate

HRID 70314

반응식

HRID 70314 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][C:3]=1[CH3:19].[NH2:20][C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>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].COCCOC>[NH2:20][C:21]([C:23]1[CH:28]=[C:27]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][C:3]=2[CH3:19])[CH:26]=[CH:25][CH:24]=1)=[O:22]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2737814(3-Carbamoylphenyl)boronic acidHCID 593164611,1-Dimethylethyl {2-[(4-bromo-3-methylphenyl)oxy]ethyl}carbamate

생성물 1

HCID 593163811,1-Dimethylethyl (2-{[3'-(aminocarbonyl)-2-methyl-4-biphenylyl]oxy}ethyl)carbamate

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

A mixture of 1,1-dimethylethyl {2-[(4-bromo-3-methylphenyl)oxy]ethyl}carbamate (0.102 g, 0.31 mmol; Example V-15), 3-(aminocarbonyl)phenylboronic acid (0.056 g; 0.34 mmol), PdCl2(dppf).CH2Cl2 (0.0075 g; 0.01 mmol), DME (2 mL) and 2M Na2CO3 (2 mL) was degassed by sparging with N2,(5-10 min) then stirred at 80° C. for 5.5 h. Upon cooling, the mixture was diluted with EtOAc washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless foam. LC/MS (method A) 2.59 min, m/z 371 (M+1, 2%), 392 (M+Na, 53%), 271 ([M−Boc]+H, 100%).

후처리

  1. customby sparging with N2,(5-10 min)
  2. temperatureUpon cooling
  3. additionthe mixture was diluted with EtOAc
  4. washwashed (water, brine)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-48addb1084d54c4889c0e9cb3eea88f2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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