Bromide ion → 4-(2-Methyl-[1,3]dioxolan-2-yl)-2-(3-nitro-pyrazol-1-ylmethyl)-thiazole

HRID 2065041Notes

Reaction equation

HRID 2065041 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[N:10]=[C:11]([CH2:14]OS(C)(=O)=O)[S:12][CH:13]=2)[O:8][CH2:7][CH2:6][O:5]1.[N+:20]([C:23]1[NH:27][N:26]=[CH:25][CH:24]=1)([O-:22])=[O:21].C([O-])([O-])=O.[K+].[K+].[Br-]>CC(C)=O.CC(=O)OCC.O>[CH3:3][C:4]1([C:9]2[N:10]=[C:11]([CH2:14][N:26]3[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[N:27]3)[S:12][CH:13]=2)[O:5][CH2:6][CH2:7][O:8]1

Participants

9

Reactant 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 1234193-NitropyrazoleHCID 86650891Methanesulfonic acid 4-(2-methyl-[1,3]dioxolan-2-yl)thiazol-2-ylmethyl ester

Product 1

HCID 669291444-(2-Methyl-[1,3]dioxolan-2-yl)-2-(3-nitro-pyrazol-1-ylmethyl)-thiazole

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 4-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl ester (320 mg, 1.15 mmol) in acetone (6.0 mL) was added to a solution of 5-nitro-1H-pyrazole (136 mg, 1.20 mmol) in acetone (6.0 mL). K2CO3 (800 mg, 5.73 mmol) followed by TBA bromide (741 mg, 0.23 mmol) were added and the reaction mixture was stirred at rt overnight. Water (10 mL) and EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (2:1 hept-EA)=0.10. LC-MS-conditions 01: tR=0.81 min, [M+H]+=296.90.

Workup

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (10 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (2:1 hept-EA)

Sources & evidence

ORD record
ord-0d91714725b944c8a0aae4b1a1c92fdb
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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