Potassium Hydroxide → 2-[2-(3-Bromophenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

HRID 1788520Notes

Reaction equation

HRID 1788520 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](O)=[C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[N:22]([CH:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)[C:21]5[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=5[N:19]=4)[CH:14]=3)[N:9]=2)[CH:7]=1.BrC1C=C(C(=O)C)C=CC=1.[OH-].[K+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[N:22]([CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]5)[C:21]5[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=5[N:19]=4)[CH:14]=3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 165023'-BromoacetophenoneHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 52761012-[2-(3-Bromophenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acidYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Following the procedure and workup for Compound 354, Compound 354e (100 mg, 0.256 mmol) was reacted with 1-(3-bromo-phenyl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (15 mg, 12% yield).

Sources & evidence

ORD record
ord-820f8c9b27db46b497cd74a95f2eba26
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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