Tetrahydrofuran → HCID 86613581, compound

HRID 1983175Notes

Reaction equation

HRID 1983175 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[O:9][C:10]([C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][O:16][C:17]=3[CH3:18])=[N:11][N:12]=2)=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[H-].[Na+].[O:28]1CCC[CH2:29]1>CO.ClCCl>[Cl:1][C:2]1[C:7]([C:8]2[O:9][C:10]([C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][O:16][C:17]=3[CH3:18])=[N:11][N:12]=2)=[CH:6][CH:5]=[C:4]([O:28][CH3:29])[N:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86613580HCID 86613580, compound

Product 1

HCID 86613581HCID 86613581, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dichloro-3-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridine (316 mg, 0.85 mmol) in tetrahydrofuran (3 mL) and methanol (3 mL) was added sodium hydride (55% dispersion in mineral oil, 41 mg, 0.93 mmol) and the reaction mixture was stirred for 4 h at ambient temperature. The resulting suspension was diluted with dichloromethane (10 mL) and was washed brine (half saturated, 10 mL). The aqueous layers were extracted with dichloromethane (10 mL) and dried over sodium sulfate. The filtrate was treated with tert-butylmethylether (20 mL) and the dichloromethane was distilled off. The resulting suspension was stirred for 5 min, filtered off and washed with tert-butylmethylether affording the title compound (51 mg, 16%) which was obtained as a white solid. MS: m/e=369.0 [M+H]+.

Workup

  1. washwas washed brine (half saturated, 10 mL)
  2. extractionThe aqueous layers were extracted with dichloromethane (10 mL)
  3. dry with materialdried over sodium sulfate
  4. additionThe filtrate was treated with tert-butylmethylether (20 mL)
  5. distillationthe dichloromethane was distilled off
  6. stirringThe resulting suspension was stirred for 5 min
  7. filtrationfiltered off
  8. washwashed with tert-butylmethylether affording the title compound (51 mg, 16%) which
  9. customwas obtained as a white solid

Sources & evidence

ORD record
ord-1dfb1ce93050420ea7afde613ac29e64
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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