Hydrochloric Acid → HCID 67530164, compound

HRID 2388210Notes

Reaction equation

HRID 2388210 reaction equation
[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:4]=2[C:5](I)=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:22]([Cu])#[N:23].[OH-].[NH4+].Cl>CCOC(C)=O.CN1CCCC1=O>[C:22]([C:5]1[C:4]2[C:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[N:15][O:16][C:3]=2[C:2]([OH:1])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)#[N:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86648122HCID 86648122, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67530164HCID 67530164, compoundYield 57.9%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

Ethyl 7-hydroxy-4-iodo-3-(thiophen-2-yl)isoxazolo[4,5-c]pyridine-6-carboxylate (310 mg, 0.745 mmol) and CuCN (200 mg, 2.24 mmol) were added to 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 136 mg of the title compound. MS: (+) m/z 316.29 (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-73fc1f4e196249cda7f655e9830bc9f2
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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