Sodium Carbonate → HCID 21897346, compound

HRID 720005Notes

Reaction equation

HRID 720005 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.[C:9]([C:11]1[S:15][C:14](B(O)O)=[CH:13][CH:12]=1)#[N:10].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.C(OCC)(=O)C.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>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:14]2[S:15][C:11]([C:9]#[N:10])=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 41987435-Cyanothiophene-2-boronic acid

Product 1

HCID 21897346HCID 21897346, compoundYield 14.1%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-amino-5-bromopyrazine (300 mg, 1.724 mmol), dichlorobis(triphenylphosphine)palladium(II) (175 mg, 0.249 mmol), 5-cyanothiophene-2-boronic acid acid (540 mg, 3.53 mmol) and a saturated aqueous sodium carbonate solution (2 mL) in ethylene glycol dimethyl ether (5 mL) and ethanol (5 mL) was heated under reflux overnight. The reaction mixture was cooled, diluted with ethyl acetate, and washed with water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 2/3 to 1/9 hexanes/ethyl acetate) afforded 5-(5-amino-pyrazin-2-yl)-thiophene-2-carbonitrile (49.1 mg, 14.1%) as a yellow solid: LRMS for C9H6N4S (M+H)+ at m/z=203.

Workup

  1. temperatureunder reflux overnight
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d03ef31c9d54ccb858e648c7f7d4146
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

Loading…