Triethylamine → HCID 57444730, compound

HRID 861139Notes

Reaction equation

HRID 861139 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[N:19]O)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CS(Cl)(=O)=O.C(N(CC)CC)C.C(OCC)(=O)C>C(COC)OC.[Fe](Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[N:13]3[N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 8471Triethylamine3×HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 73413426HCID 73413426, compound

Product 1

HCID 57444730HCID 57444730, compoundYield 9.1%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 1-(3-bromo-4-methoxyphenyl)-2-(6-chloro-2-pyridinyl)ethanone oxime (1.00 g, 2.8 mmol) in dimethoxyethane (30 mL) at 0° C. was added slowly methylsulfonyl chloride (0.24 mL, 3.08 mmol). The reaction was stirred for 15 minutes and then triethylamine (1.7 mL, 12.3 mmol) in dimethoxyethane (3 mL) was added to the reaction. Upon addition of the triethylamine a precipitate formed. Once the addition of the triethylamine solution had been completed the reaction mixture was allowed to warm to room temperature and was stirred for 1 hour. The precipitate was removed by filteration and the precipitate was washed with dimethoxyethane. To the combined filtrate was added iron (II) chloride (14 mg, 0.12 mmol) and the resulting mixture was heated at 80° C. for 15 hours. The reaction mixture was allowed to cool to room temperature. Ethyl acetate was added to dilute the mixture and the organic phase was washed with water, brine and dried (magnesium sulfate). Filtration and concentration of the filtrate, followed by flash chromatography (4:6 ethyl acetate:hexanes) gave 2-(3-bromo-4-methoxyphenyl)-7-chloropyrazolo[1,5-a]pyridine (86 mg, 9%). 1H NMR (CDCl3): δ 8.21 (d, 1H), 7.95 (d, 1H), 7.48 (d, 1H), 7.10 (t, 1H), 6.98 (d, 1H), 6.88 (d, 1H), 6.84 (s, 1H), 3.96 (s, 3H); MS m/z 337 (M+1).

Workup

  1. customformed
  2. stirringwas stirred for 1 hour
  3. customThe precipitate was removed by filteration
  4. washthe precipitate was washed with dimethoxyethane
  5. temperaturethe resulting mixture was heated at 80° C. for 15 hours
  6. temperatureto cool to room temperature
  7. additionto dilute the mixture
  8. washthe organic phase was washed with water, brine
  9. dry with materialdried (magnesium sulfate)
  10. filtrationFiltration and concentration of the filtrate

Sources & evidence

ORD record
ord-6990debee13242db8e463ff0258641da
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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