2-(3-fluorophenyl)-1H-imidazole → 6-chloro-2-{[2-(3-fluorophenyl)-1H-imidazol-1-yl]methyl}-3-propylimidazo[1,2-a]pyridine

HRID 586374Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:14][C:15]1[N:16]=[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]2[C:24]=1[CH2:25][CH2:26][CH3:27].CO.C(Cl)Cl>CC(N(C)C)=O.CCOC(C)=O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:24]([CH2:25][CH2:26][CH3:27])=[C:15]([CH2:14][N:12]3[CH:11]=[CH:10][N:9]=[C:8]3[C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[N:16]=2)[CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Kt-BuO (0.69 mL of 1 M in THF, 0.69 mmol) is added to a solution of 3-fluoro-(1H-imidazol-2-yl)benzene (88 mg, 0.58 mmol) in anhydrous DMA (1 mL). After 15 minutes, 2-chloromethyl-6-chloro-3-(1-propyl)-imidazolo[1,2-a]pyridine (140 mg, 0.58 mmol) is added and the reaction mixture is stirred and heated at 60° C. for 15 minutes. The reaction mixture is diluted with EtOAc (10 mL), washed with water (3 mL), brine (3 mL), dried over Na2SO4, filtered and evaporated at reduced pressure to obtain a yellow solid. Sequential chromatography on silica gel eluting with EtOAc and then 5%MeOH/CH2Cl2 provides 6-chloro-2-{[2-(3-fluoropheny)-1H-imidazol-1-yl]methyl}-3-propylimidazo[1,2-a]pyridine as a cream-colored yellow solid. TLC (10% MeOH/CH2Cl2) Rf=0.35.

Workup

washwashed with water (3 mL), brine (3 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated at reduced pressure
customto obtain a yellow solid

Sources & evidence

ORD record: ord-8d638e36cfbd4aaab052ecb27541dd34
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936617B2

Reaction notes

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