Methyl iodide → HCID 22065109, compound

HRID 1835391Notes

Reaction equation

[CH2:1]([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1[N:18]=[C:17]([C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)[S:21][C:20]=2Br)[N:16]([CH3:36])[N:15]=1.IC.[Cl-].[NH4+]>C1COCC1.O>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1[N:18]=[C:17]([C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)[S:21][C:20]=2[CH3:1])[N:16]([CH3:36])[N:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyllithium (2.5 N in hexanes, 0.25 mL, 0.4 mmol) was added to a solution of 3-(2-chloro-6-fluorophenyl)-5-[2-bromo-5-(4-trifluoromethoxyphenyl)thien-3-yl]-1-methyl-1H-1,2,4-triazole (190 mg, 0.3 mmol) in dry THF (2 mL) at −75° C. and stirred for 1 hour. Iodomethane (66 mg, 29 μL, 0.5 mmol) was added to this reaction mixture and stirred at −75° C. for 30 minutes. After warming to 0° C., saturated aqueous ammonium chloride (2 mL) was added, followed by water (30 mL) and the mixture was extracted with ether (3×10 mL). The combined ethereal extracts were washed with water (30 mL) and brine (10 mL), dried over magnesium sulphate and chromatographed on silica to give the product (49 mg, 29%) as a yellow solid: mp 153-155° C.; 1H NMR (CDCl3) δ 7.59 (d, 2H), 7.29-7.39 (m, 3H), 7.25 (d, 2H), 7.12 (t, 1H), 4.01 (s, 3H), 2.62 (s, 3H); EI/MS 467 m/e (M−1).

Workup

stirringstirred at −75° C. for 30 minutes
extractionthe mixture was extracted with ether (3×10 mL)
washThe combined ethereal extracts were washed with water (30 mL) and brine (10 mL)
dry with materialdried over magnesium sulphate
customchromatographed on silica

Sources & evidence

ORD record: ord-d5ae9ae5fb754f44a18c120db07242ad
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770665B2

Reaction notes

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