Phenol → HCID 19385701, compound

HRID 1492600Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].CC(C)=O.C1(O)C=CC=CC=1.[CH3:18][C:19]1[N:24]=[C:23]2[N:25]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([CH2:38][CH2:39][CH3:40])[CH:32]=3)[C:26]([CH2:28][CH3:29])=[N:27][C:22]2=[C:21]([CH3:41])[CH:20]=1.Br[CH:43]([C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=1)[C:44]([O:46][CH3:47])=[O:45]>>[C:44]([CH:43]([C:48]1[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=1)[O:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:25]2[C:23]3=[N:24][C:19]([CH3:18])=[CH:20][C:21]([CH3:41])=[C:22]3[N:27]=[C:26]2[CH2:28][CH3:29])=[CH:32][C:33]=1[CH2:38][CH2:39][CH3:40])([O:46][CH3:47])=[O:45]

Participants

Reactant 4

HCID 996Phenol

HCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

HCID 19385672HCID 19385672, compound

HCID 86600397Acetone potassium carbonate

Product 1

HCID 19385701HCID 19385701, compoundYield 50%

Procedure

Using the K2CO3 /acetone conditions for phenol alkylation described in Step A of Example 4; 5,7-dimethyl-2-ethyl-3-[4-hydroxy-3-propylphenyl methyl]-3H-imidazo[4,5-b]pyridine (Step A, Example 8) was alkylated with methyl 2-bromo-2-(4-chlorophenyl)acetate. Standard workup and purification by flash chromatography afforded a 50% yield of the title compound.

Workup

customStandard workup and purification by flash chromatography

Sources & evidence

ORD record: ord-f2f5376b54674ad389a6f43866599a4f
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374638

Reaction notes

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