Sodium hydride → [6-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)naphthalen-2-yl]acetic acid ethyl ester

HRID 481406Notes

Reaction equation

HRID 481406 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:6]([N:13]=1)=[N:7][C:8]([CH3:12])=[CH:9][C:10]=2[CH3:11])[CH3:2].[H-].[Na+].[CH2:16]([O:18][C:19](=[O:33])[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH2:31]Br)[CH:27]=2)[CH:22]=1)[CH3:17]>CN(C=O)C.CCOC(C)=O>[CH2:16]([O:18][C:19](=[O:33])[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH2:31][N:13]3[C:6]4=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]4[N:4]=[C:3]3[CH2:1][CH3:2])[CH:27]=2)[CH:22]=1)[CH3:17]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 54418685(6-Bromomethylnaphthalen-2-yl)acetic acid ethyl ester2×

Product 1

HCID 67667088[6-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)naphthalen-2-yl]acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-ethyl-5,7-dimethylimidazo[4,5-b]pyridine (7) (1.38 g, 6.5 mmol) in 4 ml DMF was added sodium hydride (250 mg, 6.5 mmol) and the reaction mixture was stirred 15 minutes at ambient temperature. The product of Step 2, above (51) (3.07 mmol), was dissolved in 3 ml DMF and added to the reaction mixture and stirred at ambient temperature for 16 hours. The reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate solution and brine. The combined organics were then dried over MgSO4, filtered and concentrated to dryness. The crude material was then chromatographed on silica gel using 50% EtOAc in hexanes as the eluant to yield the title compound (52) (95 mg).

Workup

  1. additionadded to the reaction mixture
  2. stirringstirred at ambient temperature for 16 hours
  3. washwashed with saturated sodium bicarbonate solution and brine
  4. dry with materialThe combined organics were then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude material was then chromatographed on silica gel using 50% EtOAc in hexanes as the eluant

Sources & evidence

ORD record
ord-783589a44bc54cce911fbc80ddaec05c
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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