1,2-Dimethoxyethane → Methyl 2-[3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-pyridinyl]benzoate

HRID 1007084노트

반응식

HRID 1007084 반응식
COCCOC.Br[C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1B(O)O)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.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]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[O:24])([CH3:21])([CH3:19])[CH3:20]

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 11894Methyl 2-bromobenzoateHCID 10999519(3-(((tert-Butoxycarbonyl)amino)methyl)pyridin-4-yl)boronic acid

생성물 1

HCID 11046130Methyl 2-[3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-pyridinyl]benzoate수율 84%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

20 ml of 1,2-dimethoxyethane were aerated with argon, and 230 mg (0.2 mmol) of Pd(PPh3)4 and 0.86 g (4 mmol) of methyl 2-bromobenzoate were added. After 10 min, 1.51 g (6 mmol) of 3-(tert-butoxycarbonylaminomethyl)pyridine-4-boronic acid and finally 4 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux under argon for 13 h, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 1.15 g (84%) of a viscous pale yellow oil were obtained. MS (ES+): m/z=343 (M+1).

후처리

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto reflux under argon for 13 h
  4. temperatureafter cooling
  5. washwashed with water
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-37d854d9b928488c9a0e76ac762d5d53
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794377B2

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