Sodium Carbonate → 7-Methyl-5-(3-methylsulfonylphenyl) imidazo[1,5-a]pyrazin-8-one

HRID 518348Notes

Reaction equation

HRID 518348 reaction equation
Br[C:2]1[N:7]2[CH:8]=[N:9][CH:10]=[C:6]2[C:5](=[O:11])[N:4]([CH3:12])[CH:3]=1.[CH3:13][S:14]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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>[CH3:12][N:4]1[CH:3]=[C:2]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([S:14]([CH3:13])(=[O:16])=[O:15])[CH:22]=2)[N:7]2[CH:8]=[N:9][CH:10]=[C:6]2[C:5]1=[O:11]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 1180225995-Bromo-7-methylimidazo[1,5-a]pyrazin-8(7h)-one

Product 1

HCID 1180216437-Methyl-5-(3-methylsulfonylphenyl) imidazo[1,5-a]pyrazin-8-oneYield 20%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of compound from Example 129, step 1 (80 mg, 0.35 mmol), (3-methylsulfonylphenyl)boronic acid (77 mg, 0.6 mmol), Na2CO3 (106 mg, 1 mmol), Pd(PPh3)2Cl2 (30.0 mg) in dioxane (3 mL) and water (0.5 mL) was stirred at 120° C. for 18 h under N2. After cooling to room temperature, the mixture was filtered, concentrated and purified by prep-HPLC to give the title compound (20.0 mg, 20%). 1H NMR (Methanol-d4 400 MHz): δ 8.70-8.65 (m, 1H), 8.30-8.20 (m, 2H), 8.16 (d, J=8.0 Hz, 1H), 8.05 (d, J=8.0 Hz, 1H), 7.88 (t, J=8.0 Hz, 1H), 7.22 (s, 1H), 3.56 (s, 3H), 3.24 (s, 3H). LCMS (M+H)+ 304.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-64fb5a1af8574ba3a28b35edc1680f86
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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