Hydrochloric Acid → HCID 67529046, compound

HRID 2388212Notes

Reaction equation

HRID 2388212 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13](I)=[N:14][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([OH:17])[C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[C:24]([Cu])#[N:25].[OH-].[NH4+].Cl>CCOC(C)=O.CN1CCCC1=O>[C:24]([C:13]1[C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][O:10][C:11]=2[C:16]([OH:17])=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:14]=1)#[N:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86648123HCID 86648123, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67529046HCID 67529046, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

Ethyl 3-(4-fluorophenyl)-7-hydroxy-4-iodoisoxazolo[4,5-c]pyridine-6-carboxylate (290 mg, 0.678 mmol) and CuCN (182 mg, 2.03 mmol) were added to 4.5 mL of N-methyl-2-pyrrolidone. The resulting suspension was heated in an oil bath (T=110° C.) for 1 h. The reaction mixture was cooled slightly and poured into a vigorously stirring mixture of ammonium hydroxide (4 mL, 15% aqueous solution) and EtOAc (100 mL). The mixture was acidified with concentrated hydrochloric acid to pH 3 and extracted with EtOAc. The combined organic layer was dried over MgSO4 and concentrated, and the residue was purified flash chromatography (0-100% EtOAc/hexanes) to afford 101 mg of the title compound. MS: (+) m/z 328.32 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled slightly
  2. additionpoured into
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customthe residue was purified flash chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7cdc6774b69745db900baaa535c7a22e
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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