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Sodium Carbonate → 3-(4-quinolin-8-ylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 1044149
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HRID 1044149 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:14]2=[O:30])=[CH:9][CH:8]=1)(=O)=O.[N:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2B(O)O)[CH:36]=[CH:35][CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>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.CC#N>[N:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2[C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C:17]4=[N:18][CH:19]=[CH:20][CH:21]=[C:16]4[N:15]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[C:14]3=[O:30])=[CH:11][CH:12]=2)[CH:36]=[CH:35][CH:34]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343808-Quinolineboronic acidHCID 866606724-(2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenyl trifluoromethanesulfonate

생성물 1

HCID 585775343-(4-quinolin-8-ylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one수율 85.7%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6342Acetonitrile용매

반응 조건

온도
150 °C

실험 절차

The mixture of 4-(2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenyl trifluoromethanesulfonate (500 mg), 8-quinolineboronic acid (265 mg), Pd(Ph3P)4 (35.4 mg), 2 M Na2CO3 (1.02 mL) and CH3CN (10 mL) was heated at 150° C. for 20 min under microwave irradiation. The mixture was diluted with sat.NaHCO3aq. at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane) to give 3-(4-quinolin-8-ylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (410 mg) as white crystals.

후처리

  1. additionThe mixture was diluted with sat.NaHCO3aq
  2. extractionat 0° C. and extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-25f5206312b647d9b3ace3e20d8fcbab
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08563575B2

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