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

HRID 2233094ノート

反応式

HRID 2233094 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-b21aa020c9324fda95a4757353edaea8
出典データセット
uspto-grants-2010_05
特許番号
US07709468B2

反応ノート

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