Triethylamine → HCID 66740913, compound

HRID 1627247Notes

Reaction equation

HRID 1627247 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:6][C:7]1[N:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:9]([SH:12])=[N:10][N:11]=1.CCN(CC)CC.[F:32][C:33]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:34]=1[CH2:35]Br>C(Cl)Cl>[F:32][C:33]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:34]=1[CH2:35][S:12][C:9]1[N:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:11][N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 178489935HCID 178489935, compound

Product 1

HCID 66740913HCID 66740913, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3,4-dimethoxybenzyl)-4-(4-fluorophenyl)-4H-1,2,4-triazole-3-thiol (119 mg, 0.345 mmol) and Et3N (53 μL, 0.379 mmol) in CH2Cl2 (1.8 mL) was added 2,6-difluorobenzyl bromide (88 mg, 0.414 mmol). After stirring 2 h, the reaction mixture was concentrated and purified by flash chromatography (30% EtOAc/hexanes) to yield the title product (107 mg, 66%) as a white foam. 1H NMR (400 MHz, (CD3)2CO) δ 7.25 (m, 1H), 7.10 (m, 2H), 6.98 (m, 2H), 6.84 (m, 2H), 6.63 (d, J=8.2 Hz, 1H), 6.4 (d, J=2.0 Hz, 1H), 6.31 (m, 1H), 4.45 (s, 2H), 3.82 (s, 2H), 3.61 (s, 3H), 3.54 (s, 3H); MS (EI) m/z 472.3 (MH+).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by flash chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-42d77060deb64c489920f059d08c71ec
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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