Sodium hydride → methyl 4'-[(3,5-dibutyl-1H-1,2,4-triazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylate

HRID 719540Notes

Reaction equation

HRID 719540 reaction equation
[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[NH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[H][H].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([O:34][CH3:35])=[O:33])=[CH:22][CH:21]=1>CN(C)C=O.CO>[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:27]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:22][CH:21]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 149557953,5-Dibutyl-1H-1,2,4-triazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 10319113methyl 4'-[(3,5-dibutyl-1H-1,2,4-triazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylateYield 4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under a static nitrogen atmosphere, 2.01 g (11.0 mmol) of solid 3,5-dibutyl-1H-1,2,4-triazole was added in small portions to 12 mmol of sodium hydride in 50 ml of dimethylformamide (DMF); stirring was continued until hydrogen evolution had ceased. The anion solution was cooled to −10° C. (ice/methanol) and treated with a solution of 3.37 g (11.0 mmol) of 4-bromomethyl-2′-methoxycarbonylbiphenyl in 20 ml of dry DMF. The reaction was allowed to warm to ambient temperature and stir overnight. Methanol (10 ml) was added to destroy any unreacted sodium hydride and the DMF was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried (MgSO4). Silica gel chromatography (Waters Prep-500A) using 40% ethyl acetate/hexane gave 2.0 g (4%) of compound as an oil: NMR (CDCl3) δ 0.90 (t, J=7 HZ, 3H), 0.94 (t, J=7 Hz, 3H), 1.28–1.47 (m, 4H), 1.62–1.80 (m, 4H), 2.63–2.75 (m, 4H), 3.63 (s, 3H), 5.27 (s, 2H), 7.13–7.18 (m, 2H), 7.25–7.35 (m, 3H), 7.37–7.44 (m, 1H), 7.48–7.55 (m, 1H), 7.80–7.85 (m, 1H).

Workup

  1. stirringstir overnight
  2. customto destroy any unreacted sodium hydride
  3. customthe DMF was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-485ad2bea0154806865a107c3d858624
Source dataset
uspto-grants-2006_11
Patent number
US07132437B2

Reaction notes

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