Bromine → HCID 22065192, compound

HRID 1828032Notes

Reaction equation

[Br:1]Br.[Br:3][CH:4]([F:35])[C:5]([F:34])([F:33])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14]([CH3:32])=[C:15]([C:18]3[N:22]([CH3:23])[N:21]=[C:20]([C:24]4[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:31])[N:19]=3)[S:16][CH:17]=2)=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:1][C:17]1[S:16][C:15]([C:18]2[N:22]([CH3:23])[N:21]=[C:20]([C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])[N:19]=2)=[C:14]([CH3:32])[C:13]=1[C:10]1[CH:9]=[CH:8][C:7]([O:6][C:5]([F:34])([F:33])[CH:4]([Br:3])[F:35])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Bromine (0.03 g, 0.2 mmol) in acetic acid (0.5 mL) was added dropwise to a solution of 5-{4-[4-(2-bromo-1,1,2-trifluoroethoxy)phenyl]-3-methylthien-2-yl}-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole (0.1 g, 0.2 mmol) in acetic acid (1 mL) at 0° C. The reaction was allowed to warm to 25° C. and stirred for 50 h. The reaction mixture was made basic with saturated aq NaHCO3 (30 mL) and extracted with ether (3×30 mL). The combined ether extracts were washed with brine, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure to give crude product. Column chromatography gave the product as a clear oil (88 mg, 77%): 1H NMR (CDCl3) δ 2.19 (s, 3H), 4.06 (s, 3H), 6.58 (dt, 1H, J=47.6, 5.1, 4.0, 4.4 Hz), 7.08–7.14 (m, 1H), 7.29–7.40 (m, 6H), EI/MS 636 m/e (M+H).

Workup

extractionextracted with ether (3×30 mL)
washThe combined ether extracts were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent removed under reduced pressure
customto give crude product

Sources & evidence

ORD record: ord-4e9de36237634213b4b578750ca012bc
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056940B2

Reaction notes

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