Pyridine → HCID 57930904, compound

HRID 1097009Notes

Reaction equation

HRID 1097009 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([O:19][CH2:20][CH3:21])[C:13]=1[C:14]1[CH:15]=[N:16][NH:17][CH:18]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:2].[CH:22]1(B(O)O)[CH2:24][CH2:23]1.N1C=CC=CC=1>C1COCC1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH:22]1([N:16]2[CH:15]=[C:14]([C:13]3[C:12]([O:19][CH2:20][CH3:21])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=3[O:3][CH2:1][CH3:2])[CH:18]=[N:17]2)[CH2:24][CH2:23]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 2760897Cyclopropylboronic acidHCID 66782724HCID 66782724, compound

Product 1

HCID 57930904HCID 57930904, compound

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 3,5-diethoxy-4-(1H-pyrazol-4-yl)benzoate (20 mg), cyclopropylboronic acid (24 mg) in THF (2 ml) were added Cu(OAc)2 (37 mg), pyridine (45 ul) and TEA (48 ul) at room temperature and irradiated with microwave at 120° C. for 15 min. After cooling to room temperature, the mixture was diluted with EtOAc, filtered through celite pad and the filtrate was evaporated under reduced pressure. The residue was purified by p-TLC (hexane/EtOAc) to give the title product as a colorless solid.

Workup

  1. customirradiated with microwave at 120° C. for 15 min
  2. filtrationfiltered through celite pad
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by p-TLC (hexane/EtOAc)

Sources & evidence

ORD record
ord-f0499e176d2c4b12877c93cb7a329982
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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