631897-38-6|5-Iodo-2,4-dimethyl-1H-imidazole| Ambeed

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CAS No. :	631897-38-6
Formula :	C₅H₇IN₂
M.W :	222.03
SMILES Code :	CC1=NC(C)=C(I)N1
MDL No. :	MFCD27926672

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Yield	Reaction Conditions	Operation in experiment
50%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 20 - 90℃; for 18h;Inert atmosphere;	Compound 50.3. Methyl 4-chloro-3-(2,4-dimethyl-lH-imidazol-5-yl)benzoate. To methyl 4-chloro-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 50.2, 600 mg, 2.02 mmol) in dioxane (20 mL) was added 5-iodo-2,4-dimethyl-lH-imidazole (compound 5.5, 538 mg, 2.42 mmol) and Pd(dppf)Cl2*DCM (165 mg, 0.20 mmol). The mixture was degassed with argon and stirred for 10 minutes at room temperature, then an aqueous potassium carbonate solution (1M, 10 mL) was added and the mixture was stirred at 90 C for 18 h. The mixture was cooled and diluted with EtOAc, then filtered through Celite. The filtrate was washed with brine, dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (Si02; 0-100 % EtOAc in hexanes) to yield 270 mg (50 %) of the title compound as a foam, m/z (ES+) 265 (M+H)+. NMR (400 MHz, Chloroform-d) δ 8.07 (d, J = 2.2 Hz, 1H), 7.90 (dd, J= 8.4, 2.2 Hz, 1H), 7.50 (d, J= 8.4 Hz, 1H), 3.91 (s, 3H), 2.40 (s, 3H), 2.19 (s, 3H).
50%		Compound 50.3. Methyl 4-chloro-3-(2,4-dimethyl-lH-imidazol-5-yl)benzoate. To methyl 4-chloro-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (compound 50.2, 600 mg, 2.02 mmol) in dioxane (20 mL) was added 5-iodo-2,4-dimethyl-lH- imidazole (compound 5.5, 538 mg, 2.42 mmol) and Pd(dppf)Cl2*DCM (165 mg, 0.20 mmol). The mixture was degassed with argon and stirred for 10 minutes at room temperature, then an aqueous potassium carbonate solution (1M, 10 mL) was added and the mixture was stirred at 90 C for 18 h. The mixture was cooled and diluted with EtOAc, then filtered through Celite. The filtrate was washed with brine, dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (S1O2; 0-100 % EtOAc in hexanes) to yield 270 mg (50 %) of the title compound as a foam, m/z (ES+) 265 (M+H)+. XH NMR (400 MHz, Chloroform-d) δ 8.07 (d, J= 2.2 Hz, 1H), 7.90 (dd, J= 8.4, 2.2 Hz, 1H), 7.50 (d, J= 8.4 Hz, 1H), 3.91 (s, 3H), 2.40 (s, 3H), 2.19 (s, 3H).

Yield	Reaction Conditions	Operation in experiment
77%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 26h;Inert atmosphere;	Compound 5.6. Methyl 3-(2,4-dimethyl-lH-imidazol-5-yl)-4-methylbenzoate. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 3.56 g, 12.9 mmol), 5-iodo-2,4-dimethyl-lH-imidazole (compound 5.5, 3.43 g, 15.4 mmol), K2C03 (5.33 g, 38.6 mmol) and PdCl2(dppf CH2Cl2 (1.05 g, 1.29 mmol) were added to a round bottom flask. The flask was purged with argon, then dioxane (70 mL) and water (20 mL) were added and the mixture was heated at 90 C for 16 hours. The mixture was cooled then additional K2C03 (1M, 25 mL, 25.0 mmol) and catalyst PdCl2(dppf CH2Cl2 (l .Og, 1.2 mmol) were added. The mixture was heated at 90 C for an additional 10 hours, then cooled to room temperature and filtered through Celite. The solvent was removed under reduced pressure and the residue was cooled to 0 C and acidified to pH 3-4 with aqueous HCl (2 M). The acidic mixture was washed with EtOAc (150 mL) and then the aqueous material was adjusted to pH 10-1 1 with aqueous sodium hydroxide (2 M) and extracted with EtOAc (5 x 200 mL). The combined organic phases were dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (DCM to 5% MeOH in DCM) to yield the title compound as a thick brown oil (2.42 g, 77%). m/z (ES+) 245(M+H)+. NMR (400 MHz, CDC13) delta 7.89-7.87 (m, 2H), 7.31 (d with fine str, J= 8.6 Hz, 1 H
77%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 26h;Inert atmosphere;	Compound 5.6. Methyl 3-(2,4-dimethyl-lH-imidazol-5-yl)-4-methylbenzoate. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 3.56 g, 12.9 mmol), 5 -iodo-2,4-dimethyl-lH- imidazole (compound 5.5, 3.43 g, 15.4 mmol), K2C03 (5.33 g, 38.6 mmol) and PdCl2(dppf CH2Cl2 (1.05 g, 1.29 mmol) were added to a round bottom flask. The flask was purged with argon, then dioxane (70 mL) and water (20 mL) were added and the mixture was heated at 90 C for 16 hours. The mixture was cooled then additional K2C03 (1M, 25 mL, 25.0 mmol) and catalyst PdCl2(dppf CH2Cl2 (l.Og, 1.2 mmol) were added. The mixture was heated at 90 C for an additional 10 hours, then cooled to room temperature and filtered through Celite. The solvent was removed under reduced pressure and the residue was cooled to 0 C and acidified to pH 3-4 with aqueous HCl (2 M). The acidic mixture was washed with EtOAc (150 mL) and then the aqueous material was adjusted to pH 10-1 1 with aqueous sodium hydroxide (2 M) and extracted with EtOAc (5 x 200 mL). The combined organic phases were dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (DCM to 5% MeOH in DCM) to yield the title compound as a thick brown oil (2.42 g, 77%). m/z (ES+) 245(M+H)+. XH NMR (400 MHz, CDC13) delta 7.89-7.87 (m, 2H), 7.31 (d with fine str, J Hz, 1H), 3.89 (s, 3H), 2.38 (s, 3H), 2.31 (s, 3H), 2.11 (s, 3H).

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CAS No.: 631897-38-6

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CAS No.: 631897-38-6

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Precautionary Statements-General
Code	Phrase
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Prevention
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Health hazards
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