1,2-Dimethoxyethane → 2-(4-Fluorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrazine

HRID 2233094노트

반응식

HRID 2233094 반응식
Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+].COCCOC>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.O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:3]2[N:4]=[C:5]3[CH:10]=[N:9][CH:8]=[CH:7][N:6]3[C:2]=2[C:21]2[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=2)=[CH:12][CH:13]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 498448783-Bromo-2-(4-fluorophenyl)imidazo[1,2-a]pyrazine

생성물 1

HCID 574387672-(4-Fluorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrazine수율 27.8%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

To a 25 mL round bottom flask charged with 3-bromo-2-(4-fluorophenyl)-imidazo[1,2-a]pyrazine (Preparation #5, 0.090 g, 0.31 mmol), 4-pyridineboronic acid (0.045 g, 0.37 mmol), Pd(PPh3)4 (0.018 g, 0.015 mmol) and Cs2CO3 (0.250 g, 0.77 mmol) was added DME (10 mL) followed by water (1 mL). The reaction was allowed to stir at ambient temperature for about 3 minutes followed by submersion into an oil bath which was at about 90° C. After about 16 h, the reaction was concentrated in-vacuo and then purified by RP-HPLC (Table 1, Method d). The pure fractions were combined, concentrated, and lyophilized for about 12 h to give the title compound as a white solid (0.025 g, 23%): LC/MS (Table 1, Method b) Rt=1.54 min; MS m/z: 291.2 (M+H)+.

후처리

  1. customfollowed by submersion into an oil bath
  2. customwas at about 90° C
  3. waitAfter about 16 h
  4. concentrationthe reaction was concentrated in-vacuo
  5. custompurified by RP-HPLC (Table 1, Method d)
  6. concentrationconcentrated
  7. waitlyophilized for about 12 h

출처 및 근거

ORD 기록
ord-b21aa020c9324fda95a4757353edaea8
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709468B2

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