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Sodium hydride → 2-cyclopropyl-3-(2'-methoxycarbonylbiphenyl-4-yl)methyl-7-methyl-3H-imidazo[4,5-b]pyridine

HRID 488007
Notes
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Reaction equation

HRID 488007 reaction equation
[CH:1]1([C:4]2[NH:13][C:7]3=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]3[N:5]=2)[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28][CH3:29])=[O:27])=[CH:20][CH:19]=1.[Cl-].[NH4+]>CN(C)C=O>[CH:1]1([C:4]2[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=4[C:26]([O:28][CH3:29])=[O:27])=[CH:20][CH:19]=3)[C:7]3=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]3[N:5]=2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178428356HCID 178428356, compound

Product 1

HCID 110367292-cyclopropyl-3-(2'-methoxycarbonylbiphenyl-4-yl)methyl-7-methyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

1.64 g of 2-cyclopropyl-7-methyl-3H-imidazo[4,5-b]pyridine dissolved in 30 ml of dimethylformamide was dropwise added to 400 mg of sodium hydride. The mixture was stirred at room temperature for 30 min, and 3.1 g of methyl 2-(4-bromomethylphenyl)benzoate dissolved in 20 ml of dimethylformamide was dropwise added thereto. The mixture was stirred for 10 min and then cooled, and an aqueous ammonium chloride solution was added thereto. The mixture was extracted with ethyl acetate. The extract was washed thrice with water, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to column chromatography (chloroform:ethanol=99:1). The first eluted isomer was the title compound (yield: 1.32 g).

Workup

  1. additionwas dropwise added
  2. stirringThe mixture was stirred for 10 min
  3. temperaturecooled
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extract was washed thrice with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-068a61805dd141f18813c64212fdac28
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05298518

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes