Methyl iodide → HCID 22065186, compound

HRID 1835387Notes

Reaction equation

HRID 1835387 reaction equation
[CH2:1]([Li])CCC.[Br:6][C:7]1[C:8]([CH3:27])=[C:9]([C:13]2[N:17]([CH3:18])[N:16]=[C:15]([C:19]3[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[N:14]=2)[S:10][C:11]=1Br.IC.[Cl-].[NH4+]>C1COCC1>[Cl:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([F:25])[C:19]=1[C:15]1[N:14]=[C:13]([C:9]2[S:10][C:11]([CH3:1])=[C:7]([Br:6])[C:8]=2[CH3:27])[N:17]([CH3:18])[N:16]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 11317247HCID 11317247, compoundHCID 178418339Butyllithium

Product 1

HCID 22065186HCID 22065186, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

n-Butyllithium (0.7 g, 10.8 mmol) was added dropwise to a solution of 5-(4,5-dibromo-3-methylthien-2-yl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole (5 g, 10.8 mmol) in THF (70 mL) at −70° C. and stirred for 1 hour. Iodomethane (1.6 g, 11.29 mmol) was added to the reaction mixture and allowed to warm to 25° C. After adding saturated aq ammonium chloride (10 mL), the organic layer was separated, washed with water, followed by saturated aq sodium chloride (20 mL) and dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed to give the product as a yellow oil (2.0 g, 47%): 1H NMR (CDCl3) δ 2.32 (s, 3H), 2.48 (s, 3H), 3.99 (s, 3H), 7.07-7.13 (m, 1H), 7.28-7.38 (m, 2H); EI/MS 400 m/e (M+); Calcd. for C15H12ClBrFN3S: C, 44.96; H, 3.02; N, 10.49; Found: C, 44.94; H, 3.01; N, 10.29.

Workup

  1. customthe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-e562e8bf508047e8a06a4a8ddf18a45a
Source dataset
uspto-grants-2004_08
Patent number
US06770665B2

Reaction notes

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