Bromide ion → 5-(2-Methyl-[1,3]dioxolan-2-yl)-2-(3-nitro-pyrazol-1-ylmethyl)-oxazole

HRID 2065082

반응식

HRID 2065082 반응식
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[CH:6][N:7]=1.[N+:14]([C:17]1[NH:21][N:20]=[CH:19][CH:18]=1)([O-:16])=[O:15].[Br-].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:13][C:8]1([C:5]2[O:4][C:3]([CH2:2][N:20]3[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[N:21]3)=[N:7][CH:6]=2)[O:12][CH2:11][CH2:10][O:9]1

참가 물질

6

반응물 4

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 1234193-NitropyrazoleHCID 669290402-Chloromethyl-5-(2-methyl-[1,3]dioxolan-2-yl)-oxazole

생성물 1

HCID 669289595-(2-Methyl-[1,3]dioxolan-2-yl)-2-(3-nitro-pyrazol-1-ylmethyl)-oxazole

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-oxazol-2-yl]-methanol (35 mg, 0.19 mmol) in dry CH2Cl2 (1.0 mL) was treated at 0° C. with Et3N (0.03 mL, 0.25 mmol) followed by DMAP (2.3 mg, 0.02 mmol) and Ms-Cl (0.02 mL, 0.23 mmol). After stirring at rt for 30 min, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give crude 2-chloromethyl-5-(2-methyl-[1,3]dioxolan-2-yl)-oxazole as a yellow oil. A solution of this crude 2-chloromethyl-5-(2-methyl-[1,3]dioxolan-2-yl)-oxazole (38 mg, 0.19 mmol) in acetone (1.0 mL) was treated with 5-nitro-1H-pyrazole (21 mg, 0.19 mmol) and TBA bromide (12 mg, 0.04 mmol) followed by K2CO3 (77 mg, 0.56 mmol). The reaction mixture was stirred at rt until completion. The solvent was removed under reduced pressure and water (10 mL) followed by 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 (4:6 hept-EA) gave the title compound as a colorless oil. TLC: rf (4:6 hept-EA)=0.15. LC-MS-conditions 02: tR=0.83 min; [M+H]+=281.05.

후처리

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

출처 및 근거

ORD 기록
ord-c010daf5ea5e428f95747fcbc94ade7d
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288419B2

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