Lithium Chloride → HCID 59370289, compound

HRID 705102Notes

Reaction equation

HRID 705102 reaction equation
[Cl-].[Li+].[CH3:3][O:4][C:5](=[O:29])[C:6]1[CH:11]=[C:10]([Sn](CCC)(CCC)CCC)[CH:9]=[C:8]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=2)[CH:7]=1.[CH:30]([C:33]1[C:34](OS(C(F)(F)F)(=O)=O)=[N:35][S:36][N:37]=1)([CH3:32])[CH3:31]>C1COCC1.[Pd]>[CH3:3][O:4][C:5](=[O:29])[C:6]1[CH:7]=[C:8]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=2)[CH:9]=[C:10]([C:34]2[C:33]([CH:30]([CH3:32])[CH3:31])=[N:37][S:36][N:35]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 66754212HCID 66754212, compoundHCID 86642533HCID 86642533, compound

Product 1

HCID 59370289HCID 59370289, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium chloride (0.094 g) and palladium II tetrakis(triphenylphosphine) (0.048 g) were suspended in dry THF under nitrogen atmosphere. To this suspension was added a solution of 3-(5-Methyl-pyridin-2-yl)-5-tripropylstannanyl-benzoic acid methyl ester (0.656 g, 1.27 mmol) and trifluoro-methanesulfonic acid 4-isopropyl-[1,2,5]thiadiazol-3-yl ester (0.26 g, 0.942 mmol) in 6 mL of dry THF. The reaction mixture was heated to reflux for 70 hours. The reaction mixture was cooled to room temperature and ice water was added. After one hour the mixture was extracted with EtOAc and the combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (17:1 EtOAc/hexanes) to give 0.118 g of 3-(4-isopropyl-[1,2,5]thiadiazol-3-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester, MS (M+H)=354.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 70 hours
  3. extractionAfter one hour the mixture was extracted with EtOAc
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via flash chromatography (17:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-4839228f59934c8db8948cbbf8a27551
Source dataset
uspto-grants-2015_11
Patent number
US09173861B2

Reaction notes

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