Bromide ion → HCID 66928948, compound

HRID 2065049Notes

Reaction equation

HRID 2065049 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[S:13][C:12]([CH2:14]OS(C)(=O)=O)=[N:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[N+:20]([C:23]1[CH:24]=[N:25][NH:26][CH:27]=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[S:13][C:12]([CH2:14][N:25]3[CH:24]=[C:23]([N+:20]([O-:22])=[O:21])[CH:27]=[N:26]3)=[N:11][CH:10]=2)[O:5][CH2:6][CH2:7][O:8]1

Participants

9

Reactant 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 86649489(5-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-2-yl)methyl methanesulfonate

Product 1

HCID 66928948HCID 66928948, compound

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 5-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl ester (520 mg, 1.86 mmol) in acetone (15.0 mL) was added to a solution of 4-nitro-1H-pyrazole (221 mg, 1.96 mmol) in acetone (15.0 mL). K2CO3 (1.300 g, 9.31 mmol) followed by TBA bromide (120 mg, 0.37 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 (10:1 to 2:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (1:2 hept-EA)=0.15. LC-MS-conditions 01: tR=0.83 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 (10:1 to 2:1 hept-EA)

Sources & evidence

ORD record
ord-79a18a2ae8b04375ae926d64d2cca31b
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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