4’-[(2-butyl-4-chloro-5-hydroxymethyl)-1H-imidazol-1-yl)methyl]-[1,1’-Biphenyl]-2-carbonitrile synthesis
- Product Name:4’-[(2-butyl-4-chloro-5-hydroxymethyl)-1H-imidazol-1-yl)methyl]-[1,1’-Biphenyl]-2-carbonitrile
- CAS Number:114772-55-3
- Molecular formula:C22H22ClN3O
- Molecular Weight:379.88
83857-96-9
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Yield:114772-55-3 88%
Reaction Conditions:
Stage #1:2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde;4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile with potassium carbonate in 1-methyl-pyrrolidin-2-one at 70 - 75;
Stage #2: with sodium tetrahydroborate in 1-methyl-pyrrolidin-2-one at 30;
Stage #3: with water in 1-methyl-pyrrolidin-2-one;isopropyl alcohol at 75 - 80; for 1.5 h;
Steps:
1
Example-1 [117] [118] Preparation of 2-n-Butyl-4-chloro-l-[2'-(cyanobiphenyl-4-yl) methyl] -5-(hydroxymethyl)-imidazole (IV); [119] A mixture of 4'-Bromomethyl-2-cyanobiphenyl(II) (125.0 g), l-Methyl-2-pyrrolidinone (NMP) (375.0 ml), anhydrous potassium carbonate (76.0 g) and 2-Butyl-4-chloro-5-formylimidazole (III) (90.0 g) was heated at 7O0C to 750C for about 4-5 hrs. Sodium borohydride (18.0 g) was charged to the reaction mixture at 3O0C. Water (1875.0 ml) was added to it and isopropanol (562.5 ml) was added to the wet cake and heated at 75-8O0C for 1.5 hours. The reaction mixture was cooled at room temperature and filtered. The solid was suck dried and dried in oven to give the title compound (153.0g).[120] Yield: 88.0%[121] Purity (By HPLC): 99.1%
References:
ALEMBIC LIMITED;DEO, Keshav;DESAI, Sanjay;RATHOD, Dhiraj;PARIKH, Chirag;MOKAL, Ramesh WO2010/29457, 2010, A2 Location in patent:Page/Page column 11-12
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114772-53-1
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