Water → 3'-(4-Methanesulfonylphenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid t-butyl ester

HRID 220429Notes

Reaction equation

HRID 220429 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19](Cl)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:27][S:28]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)(=[O:30])=[O:29].O>CN(C)C(=O)C.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.COC(C)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:34]3[CH:35]=[CH:36][C:31]([S:28]([CH3:27])(=[O:30])=[O:29])=[CH:32][CH:33]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 687239983'-(4-Methanesulfonylphenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid t-butyl esterYield 86%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 15413tert-Butyl methyl etherSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
65 °C

Procedure

Dissolve 3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (6.92 g, 30.75 mmol), potassium carbonate (7.34 g, 53.09 mmol) and 4-methanesulfonylbenzeneboronic acid (5.31 g, 26.55 mmol) in N,N-dimethylacetamide (90 mL) and purge for 15 min. Add water (35 mL) and the mixture further purged for 15 min. Add tetrakis(triphenylphosphine)palladium(0) (0.130 g, 0.11 mmol) and heat for 2 hr. 10 min. at 110° C. Allow to cool to 65° C., add water (30 mL) and t-butyl methyl ether (70 mL) and stir for 0.5 hr. Filter off the solid and dry in a vacuum oven to give 3′-(4-methanesulfonylphenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (8.3 g, 86%). MS (ES): m/z=419 [M+H]+.

Workup

  1. custompurge for 15 min
  2. customAdd water (35 mL) and the mixture further purged for 15 min
  3. custom10 min.
  4. customat 110° C
  5. filtrationFilter off the solid
  6. customdry in a vacuum oven

Sources & evidence

ORD record
ord-aaf61c8f256c43dc80ea0a39df68c97e
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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