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

HRID 2233094Notes

Reaction equation

HRID 2233094 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-b21aa020c9324fda95a4757353edaea8
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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