Imidazole → HCID 58447643, compound

HRID 1036183Notes

Reaction equation

HRID 1036183 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][N:13]=2)=[O:10])=[CH:4][CH:3]=1.[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I>[N:24]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:14][N:13]=3)=[O:10])=[CH:4][CH:3]=2)[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 68247167HCID 68247167, compound

Product 1

HCID 58447643HCID 58447643, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(4-iodophenyl)-N-(5-phenylpyridin-2-yl)acetamide 53-3 (41 mg, 0.1 mmol), imidazole (10 mg, 0.15 mmol), potassium phosphate (41 mg, 0.3 mmol), CuI (2 mg, 0.01 mmol) and L-proline (2.3 mg, 0.02 mmol) in DMSO (0.5 mL) was stirred under an atmosphere of dry Argon at 100° C. for 10 hours. The crude product was purified by reverse phase HPLC to give 2-(4-(1H-imidazol-1-yl)phenyl)-N-(5-phenylpyridin-2-yl)acetamide 53 as white solid. MS m/z 355.1 (M+1); 1H NMR 400 MHz (CDCl3) δ 8.47-8.46 (m, 1H), 8.29 (d, 1H, J=8.8 Hz), 7.99 (s, 1H), 7.92 (dd, 1H, J1=16.8 Hz, J2=2.4 Hz), 7.88 (s, 1H), 7.55-7.53 (m, 2H), 7.49-7.38 (m, 6H), 7.29 (s, 1H), 7.23 (s, 1H), 3.83 (s, 2H).

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-139808efdea345b3baaa6d64ebe5aa62
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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