Sodium hydride → HCID 54352161, compound

HRID 1742412Notes

Reaction equation

HRID 1742412 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH3:17])[NH:11][C:12]=1[Cl:13])=[O:7])[CH3:4].[Br:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[CH:24](Cl)[CH2:23][CH2:22]2>O1CCOCC1>[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH3:17])[N:11]([CH:24]2[C:25]3[C:21](=[CH:20][C:19]([Br:18])=[CH:27][CH:26]=3)[CH2:22][CH2:23]2)[C:12]=1[Cl:13])=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 18950842HCID 18950842, compoundHCID 223495155-Bromo-1-chloro-2,3-dihydro-1H-indene

Product 1

HCID 54352161HCID 54352161, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
110 °C

Procedure

Sodium hydride (64 mg, 2.8 mmol) was added to 2-butyl-5-chloro-1H-imidazole-4-carboxylic acid ethyl ester (647 mg, 2.8 mmol) in anhydrous 1,4-dioxane (3 mL). After 0.25 hour, a solution of 5-bromo-1-chloro-indane (696 mg, 3.0 mmol)in dioxane (2.0 mL) was added. The reaction mixture was heated at 110° C. for 20 hours, cooled to room temperature and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using 50% ethyl acetate/hexanes to give 486 mg of a colorless oil. 1H NMR (250 MHz, d6 -DMSO): d 7.55 (s, 1 H), 7.36 (d, 1 H), 6.86 (d, 1 H), 6.10 (t, 1 H), 4.20 (q, 2 H), 3.25-2.65 (m), 1.65 (m, 2 H), 1.35 (m, 2 H), 122 (t,3H), 0.90 (t, 3 H).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was chromatographed on SiO2

Sources & evidence

ORD record
ord-d48240e58be546e38102c3b70c240bb9
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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