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Sodium Carbonate → Methyl 3-amino-6-(4-(methylsulfonyl)phenyl)pyrazine-2-carboxylate

HRID 78559
Notes
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Reaction equation

HRID 78559 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[CH3:13][S:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)(=[O:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([C:20]2[CH:21]=[CH:22][C:17]([S:14]([CH3:13])(=[O:16])=[O:15])=[CH:18][CH:19]=2)=[CH:6][N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 27343644-(Methanesulfonyl)phenylboronic acid

Product 1

HCID 51000410Methyl 3-amino-6-(4-(methylsulfonyl)phenyl)pyrazine-2-carboxylateYield 53%

Reagents, catalysts & solvents 3

HCID 6102075
Dichlorobis(triphenylphosphine)palladium
Catalyst
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (1.5 g, 6.465 mmol), (4-methylsulfonylphenyl)boronic acid (1.552 g, 7.758 mmol), bis(triphenylphosphine) palladium(II)dichloride (226.9 mg, 0.3233 mmol), and Na2CO3 (9.700 mL of 2 M, 19.40 mmol) in DME (18.75 mL) were heated in the microwave at 110° C. for 1 hour. The resultant mixture was diluted with EtOAc and washed with water. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography (50% EtOAc/hexanes) to afford the title compound (600 mg, 53% Yield).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel by flash column chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c79dc17f14994985b8414819b5254db4
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841308B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes