Ammonium Chloride → HCID 86659541, compound

HRID 522504Notes

Reaction equation

HRID 522504 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[Li+].[Cl-].I[C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=1.[NH4+].[Cl-]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[Cl:1][C:2]1[C:7]([C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=2)=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 785042,6-DichloropyrazineHCID 142891Ethyl 4-iodobenzoateHCID 433294Lithium Chloride

Product 1

HCID 86659541HCID 86659541, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

2,6-Dichloropyrazine (9) (149 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25° C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. Pd(dba)2 (17 mg, 3 mol %) and P(o-furyl)3 (14 mg, 6 mol %) dissolved in THF (2 mL), followed by the addition of ethyl 4-iodobenzoate (359 mg, 1.3 mmol), were then transferred via cannula to the reaction mixture. The reaction mixture was stirred at 25° C. for 1.5 h. with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3×50 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:2) furnished compound 11b (251 mg, 87%) as a colourless solid.

Workup

  1. extractionextracted with diethyl ether (3×50 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationAfter filtration
  4. customthe solvent was evaporated in vacuo
  5. customPurification by flash-chromatography (CH2Cl2/n-pentane, 1:2)

Sources & evidence

ORD record
ord-eb865ed860084400862cf3ed5a81e4d4
Source dataset
uspto-grants-2016_05
Patent number
US09334237B2

Reaction notes

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