Diethyl Ether → HCID 67212560, compound

HRID 1671344Notes

Reaction equation

HRID 1671344 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[CH:15]=[C:11]2[O:12][C:13]=1[CH3:14].F[B-](F)(F)F.[O:24]=[N+:25]=[O:26].CCOCC>CC#N>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([N+:25]([O-:26])=[O:24])=[C:11]2[O:12][C:13]=1[CH3:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11073463Nitronium tetrafluoroborateHCID 591860073-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole

Product 1

HCID 67212560HCID 67212560, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(2,4-dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole (Intermediate HE) (768 mg, 2.73 mmol) in MeCN (13 ml) is added nitronium tetrafluoroborate (0.5M solution in sulfolane, 6.6 ml, 3.3 mmol, 1.2 eq.). The dark orange reaction mixture is stirred at RT for 3 h then diluted into Et2O (150 ml) and washed successively with Na2CO3 1M in water (100 ml), water (100 ml) and brine (50 ml). The organic layer is dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The resulting crude residue is purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/TBME 95:5→7:3) to yield the title compound as a greenish solid. TLC: RF=0.27 (heptane/TBME 3:1); HPLC: AtRet=2.73; MS: m/z 325.8 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 2.49 (s, 3H), 2.66 (s, 3H), 7.47 (dd, J 8.3, 2.0, 1H), 7.52 (d, J 8.3, 1H), 7.64 (d, J 2.0, 1H).

Workup

  1. washwashed successively with Na2CO3 1M in water (100 ml), water (100 ml) and brine (50 ml)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe resulting crude residue is purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/TBME 95:5→7:3)

Sources & evidence

ORD record
ord-e39d3d05480e43fcb6ac668a2c9fde19
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

Loading…