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

HRID 539797
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HRID 539797 반응식
Cl[C:2]1[N: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[N: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:25])[F:27])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:21])([CH3:20])[CH3:22])[CH:16]=3)[N:10]=2)[CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

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HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 86667860N-[5-(6-chloroimidazo[1,2-a]pyrazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

생성물 1

HCID 67982904N-[5-[6-(2-fluorophenyl)imidazo[1,2-a]pyrazin-2-yl]-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide수율 10.1%

시약·촉매·용매 2

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

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온도
70 °C

실험 절차

An 8 mL vial is charged with N-[5-(6-chloroimidazo[1,2-a]pyrazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.0516 g, 0.13 mmol), 2-fluorophenylboronic acid (Combi-Blocks, 32 mg, 0.26 mmol), Na2CO3 (0.0413 g, 0.39 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.009 g, 0.01 mmol), and isopropanol-water (1 mL, 3:1). The mixture is stirred at 70° C. for 16 hr. The reaction mixture is concentrated, taken up into EtOAc and CH2Cl2 (1:1) and purified by preparative plate TLC (1:1 Hexanes:EtoAc) to give the title compound (6 mg, 10% yield). LCMS m/z=457.5 [M+H]+, tR=3.06 min. (compound same as Example 86)

후처리

  1. concentrationThe reaction mixture is concentrated
  2. custompurified by preparative plate TLC (1:1 Hexanes:EtoAc)

출처 및 근거

ORD 기록
ord-93669e03ffce41d1839b87a698d83639
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871767B2

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