Ammonium Chloride → HCID 22638594, compound

HRID 2416199Notes

Reaction equation

HRID 2416199 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[N:13]=2)[CH:6]=[CH:5][N:4]=1)[CH3:2].[F:19][C:20]1[CH:21]=[CH:22][C:23]([N+:28]([O-:30])=[O:29])=[C:24]([CH:27]=1)[CH2:25]Br.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[S:10][CH:11]=[C:12]([CH:14]([CH2:25][C:24]3[CH:27]=[C:20]([F:19])[CH:21]=[CH:22][C:23]=3[N+:28]([O-:30])=[O:29])[C:15]([O:17][CH3:18])=[O:16])[N:13]=2)[CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 105616432-(Bromomethyl)-4-fluoro-1-nitrobenzeneHCID 22638557HCID 22638557, compound

Product 1

HCID 22638594HCID 22638594, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl 2-[2-(2-ethyl-4-pyridyl)-1,3-thiazole-4-yl]acetate (520 mg, 2.0 mmol) (Example 12(a)) was dissolved in toluene and the solution was concentrated by rotary evaporation. This procedure was repeated, and the dry residue was dissolved in 18 mL anhydrous THF (18 mL). The solution was cooled to −78° C., and LHMDS (2.1 mL, 1.0 M in THF, Aldrich) was added slowly via a syringe. To the resulting red solution, 5-fluoro-2-nitrobenzyl bromide (400 mg, 1.7 mmol) was added as a solid in one portion. The reaction was warmed slowly to RT over 4 h. Saturated aqueous NH4Cl (50 mL) was added, and the mixture was extracted with 100 mL of EtOAc. The organic layer was separated, washed with H2O (100 mL), dried (Na2SO4), and concentrated. Flash chromatography (gradient elution: 10-40% EtOAc in hexanes) of the crude material afforded the title compound as a clear oil. MS m/z: 416 (M+1). Calc'd for C20H18FN3O4S: 415.10.

Workup

  1. concentrationthe solution was concentrated by rotary evaporation
  2. dissolutionthe dry residue was dissolved in 18 mL anhydrous THF (18 mL)
  3. additionLHMDS (2.1 mL, 1.0 M in THF, Aldrich) was added slowly via a syringe
  4. temperatureThe reaction was warmed slowly to RT over 4 h
  5. extractionthe mixture was extracted with 100 mL of EtOAc
  6. customThe organic layer was separated
  7. washwashed with H2O (100 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. washFlash chromatography (gradient elution: 10-40% EtOAc in hexanes) of the crude material

Sources & evidence

ORD record
ord-10339fde41cc4c6f83a37241ddc84bae
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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