Dimethylformamide → 3-[4-(1-carbomethoxy-1-cyclohexyl)methoxyphenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 2255559Notes

Reaction equation

HRID 2255559 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3=[N:14][CH:15]=[CH:16][C:17]([CH3:18])=[C:12]3[N:11]=[C:10]2[CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=1.[CH2:22]1[O:39][CH2:38]COCCOCCOCCOCCOC1.Br[CH:41]([CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1)C(OC)=O.CN(C=[O:56])C>>[C:22]([C:46]1([CH2:41][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][N:9]3[C:13]4=[N:14][CH:15]=[CH:16][C:17]([CH3:18])=[C:12]4[N:11]=[C:10]3[CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=2)[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]1)([O:39][CH3:38])=[O:56]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 2855718-Crown-6HCID 295968Methyl 2-bromo-2-cyclohexylacetateHCID 193856433-(4-hydroxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 193856563-[4-(1-carbomethoxy-1-cyclohexyl)methoxyphenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridineYield 10%

Procedure

A solution of 0.200 g (0.71 mmol) of 3-(4-hydroxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine (Step D, Example 2) dissolved in 0.5 mL of DMF was deprotonated (82 mg KH, 0.188 g 18-crown-6) and alkylated with 0.184 g (0.78 mmol) of commercially available methyl 2-bromo-2-cyclohexylacetate similarly to the procedure described in Example 2, Step E. Purification on a silica gel flash chromatography column eluted with 30% ethyl acetate/hexane afforded 0.029 g (10%) of the title compound.

Workup

  1. customPurification on a silica gel flash chromatography column
  2. washeluted with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b817ea8df2cb43aea52f1071ac476495
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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