Potassium Carbonate → Ethyl-5-bromo-4-[(1H-imidazol-2ylthio)methyl]-1-phenyl-1H-pyrazole-3-carboxylate

HRID 1521850Notes

Reaction equation

HRID 1521850 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11]Br)=[C:9]([Br:13])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:7]=1)=[O:5])[CH3:2].[SH:20][C:21]1[NH:22][CH:23]=[CH:24][N:25]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][S:20][C:21]2[NH:22][CH:23]=[CH:24][N:25]=2)=[C:9]([Br:13])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66578936Ethyl 5-bromo-4-(bromomethyl)-1-phenyl-1H-pyrazole-3-carboxylateHCID 178527877HCID 178527877, compound

Product 1

HCID 68228885Ethyl-5-bromo-4-[(1H-imidazol-2ylthio)methyl]-1-phenyl-1H-pyrazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of ethyl-5-bromo-4-(bromomethyl)-1-phenyl-1H-pyrazole-3-carboxylate (2.1 g, 5.44 mmol, 1 eq) and 2-mercaptoimidazole (0.6 g, 5.98 mmol, 1.1 eq) in ACN (30 mL) is added dry K2CO3 (2.25 g, 16.32 mmol, 3 eq) and the reaction mixture is heated at 85° C. for 1 h. The reaction mixture is diluted with DCM and filtered. The filtrate is concentrated and the residue is partitioned between DCM/water. The organic layer is dried over Na2SO4 and concentrated to afford the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 12.29 (bs, 1H), 7.59-7.53 (m, 5H), 7.16 (d, J=1.4 Hz, 1H), 6.94 (d, J=1.4 Hz, 1H), 4.28-4.26 (m, 2H), 4.19 (s, 2H), 1.29 (t, J=7.7 Hz, 3H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated
  3. customthe residue is partitioned between DCM/water
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-15e02a17aa1f477f86f18209c9622fbe
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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