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Sodium Carbonate → N-[5-[6-(2-fluorophenyl)imidazo[1,2-a]pyridin-2-yl]-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

HRID 539761
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인쇄 미리보기

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HRID 539761 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:27])([F:26])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)[N:10]=2)[CH:7]=1.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(C)C.O>[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:26])([F:27])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:20])[CH3:21])[CH:16]=3)[N:10]=2)[CH:7]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 67985680N-[5-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

생성물 1

HCID 67983503N-[5-[6-(2-fluorophenyl)imidazo[1,2-a]pyridin-2-yl]-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide수율 55%

시약·촉매·용매 2

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 21889133Propan-2-ol--water (1/1)용매

반응 조건

온도
80 °C

실험 절차

An 8 mL vial is charged with N-[5-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.044 g, 0.11 mol), (2-fluorophenyl)boronic acid (Combi-Blocks, 28 mg, 0.2 mmol), Na2CO3 (0.032 g, 0.3 mmol), bis(triphenylphosphine)palladium(II) dichloride (7 mg, 0.01 mmol) and isopropanol-water (1 mL, 3:1). The reaction mixture is stirred at 80° C. for 16 hr, then cooled, concentrated, taken into EtOAc and CH2Cl2 (1:1), filtered, concentrated onto celite and purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (25.4 mg, 55% yield). LCMS m/z=456.5 [M+H]+, tR=2.69 min. (compound same as Example 83)

후처리

  1. temperaturecooled
  2. concentrationconcentrated
  3. filtrationfiltered
  4. concentrationconcentrated onto celite
  5. custompurified by silica gel chromatography (0-100% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-3b3067a7ff6e45baa4c0ee24056a2d35
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871767B2

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