Sodium hydride → 4-{2-[2-(3,4-Dimethoxyphenyl)-vinyl]-4,7-dimethoxy-5,6-dimethyl-benzoimidazol-1-ylmethyl}-benzoic acid methyl ester

HRID 1278727Notes

Reaction equation

HRID 1278727 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]2[NH:19][C:18]3[C:20]([O:28][CH3:29])=[C:21]([CH3:27])[C:22]([CH3:26])=[C:23]([O:24][CH3:25])[C:17]=3[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Br)=[CH:35][CH:34]=1>CN(C=O)C>[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][C:36]([CH2:39][N:19]2[C:18]3[C:20]([O:28][CH3:29])=[C:21]([CH3:27])[C:22]([CH3:26])=[C:23]([O:24][CH3:25])[C:17]=3[N:16]=[C:15]2[CH:14]=[CH:13][C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH3:3])[CH:6]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 540257852-[2-(3,4-Dimethoxyphenyl)-vinyl]-4,7-dimethoxy-5,6-dimethyl-1H-benzoimidazole

Product 1

HCID 701481694-{2-[2-(3,4-Dimethoxyphenyl)-vinyl]-4,7-dimethoxy-5,6-dimethyl-benzoimidazol-1-ylmethyl}-benzoic acid methyl esterYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride, 60% dispersion in oil (150 mg; 3.5 mmol) in 20 mL of DMF, {2-[2-(3,4-dimethoxyphenyl)-vinyl]-4,7-dimethoxy-5,6-dimethyl-1H-benzoimidazole (1.2 g; 3.25 mmol) in DMF (20 mL) was added dropwise over 5 minutes. After addition, the reaction mixture was stirred at ambient temperature for 30 minutes, then methyl-4-(bromomethyl)benzoate (745 mg; 3.25 mmol) in DMF (10 mL) was added. The reaction mixture was stirred at ambient temperature for 4 hours. The DMF was concentrated to a residue, and H2O was added. The solid was collected by filtration. Recrystallization from MeOH gave 620 mg (37% yield) of the title compound as a light yellow solid, hemihydrate, m.p. 111-114° C. Anal. Calcd. for C30H32N2O6—0.5 H2O: C, 68.56, H, 6.33; N, 5.33. Found: C, 68.51; H, 6.27; N, 5.28. Mass spectrum: (EI; M+) m/z 516.1H-NMR (DMSO-d6; 400 MHz) δ7.9(d, 2H), 7.72-7.78(d, 1H), 7.31(d, 1H), 7.2-7.26 (m, 4H), 6.95 (d, 1H), 5.9 (s, 2H), 4.12 (s, 3H), 3.81 (s 3H), 3.79 (s, 3H),3.77 (s, 3H), 3.53 (s, 3H), 2.1 ppm (d, 6H).

Workup

  1. additionAfter addition
  2. stirringThe reaction mixture was stirred at ambient temperature for 4 hours
  3. concentrationThe DMF was concentrated to a residue, and H2O
  4. additionwas added
  5. filtrationThe solid was collected by filtration
  6. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-1da81ba0d7a84c73a9b7e0b41b801d16
Source dataset
uspto-grants-2002_09
Patent number
US06444694B1

Reaction notes

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