Pyrazole → HCID 44554076, compound

HRID 1254050Notes

Reaction equation

HRID 1254050 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[NH:28]1[CH:32]=[CH:31][CH:30]=[N:29]1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([N:28]3[CH:32]=[CH:31][CH:30]=[N:29]3)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 44554077HCID 44554077, compound

Product 1

HCID 44554076HCID 44554076, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
195 °C

Procedure

To a microwave tube were added 2-[5-[(4-chlorophenyl)thio]-4-(4-iodophenyl)-1-methyl-1H-imidazol-2-yl]pyridine (Example 61, 150 mg, 0.298 mmol), CuI (5.67 mg, 0.03 mmol), pyrazole (41 mg, 0.595 mmol), potassium carbonate (82 mg, 0.595 mmol), and 4 mL of NMP. The reaction was heated at 195° C. for 90 min via microwave. After filtration through Celite, the reaction mixture was purified by reverse phase HPLC to afford the title compound. 1H NMR (500 MHz, (CDCl3): 8.66 (d, 1H), 8.37 (d, 1H), 8.24 (d, 2H), 7.96 (d, 1H), 7.86 (dt, 1H), 7.76 (d, 2H), 7.54 (d, 2H), 7.53 (m, 1H), 7.33 (dd, 1H), 7.24 (d, 2H), 7.06 (d, 2H), 6.48 (m, 1H), 4.16 (s, 3H). LCMS: m/z 444 (M+H)+.

Workup

  1. filtrationAfter filtration through Celite
  2. customthe reaction mixture was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-eac1e317980e48a2a180ffbdf76d7ed6
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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