Cesium carbonate → HCID 118021401, compound

HRID 518324Notes

Reaction equation

HRID 518324 reaction equation
[NH2:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6](Br)[N:7]=1.[CH3:11][S:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)(=[O:14])=[O:13].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.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>[NH2:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([S:12]([CH3:11])(=[O:14])=[O:13])[CH:20]=2)[N:7]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 42614393HCID 42614393, compound

Product 1

HCID 118021401HCID 118021401, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-amino-5-bromo-1-methylpyrazin-2-one (81.0 mg, 0.4 mmol), (3-methylsulfonylphenyl)boronic acid (120.0 mg, 0.6 mmol), Cs2CO3 (391.0 mg, 1.2 mmol), Pd(PPh3)4 (20.0 mg, 0.017 mmol) in dioxane (20.0 mL) and water (2.0 mL) was stirred at 95° C. for 12 h under N2. The mixture was concentrated and purified by silica gel chromatography (PE: EA=3:2) to give the title compound (20.0 mg, 18%). 1H NMR (DMSO-d6 400 MHz): δ 8.35 (s, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.73 (s, 1H), 7.66 (t, J=8.0 Hz, 1H), 6.93 (brs, 2H), 3.50 (s, 3H), 3.24 (s, 3H). LCMS (M+H)+ 280.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel chromatography (PE: EA=3:2)

Sources & evidence

ORD record
ord-48e20d21db144790aa563558751b9c40
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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