Potassium Carbonate → Methyl 5-(4-benzyl-5-methoxy-4H-1,2,4-triazol-3-yl)-4-cyclopropyl-2-methylbenzoate

HRID 1487986Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([O:13][CH3:14])=[N:11][N:10]=[C:9]1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]1([C:19]2[C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([CH3:38])[CH:20]=2)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH2:1]([N:8]1[C:12]([O:13][CH3:14])=[N:11][N:10]=[C:9]1[C:28]1[C:19]([CH:16]2[CH2:18][CH2:17]2)=[CH:20][C:21]([CH3:38])=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-benzyl-3-bromo-5-methoxy-4H-1,2,4-triazole (compound 91.3, 1.2 g, 4.48 mmol), methyl 4-cyclopropyl-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 91.1, 1.56 g, 4.93 mmol), PdCl2(dppf)CH2Cl2 (0.37 g, 0.45 mmol) and potassium carbonate (3.10 g, 22.5 mmol) in dioxane (50 mL) and water (20 mL) was degassed with argon. The mixture was heated at 90° C. for 18 hours under argon, then cooled to room temperature. The mixture was diluted with ethyl acetate (300 mL) and washed with water then brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexanes:EtOAc 10:1 to 4:1) to yield 1.51 g (89%) of the title compound as thick oil. m/z (ES+) 378 (M+H)+.

Workup

customwas degassed with argon
temperaturecooled to room temperature
additionThe mixture was diluted with ethyl acetate (300 mL)
washwashed with water
dry with materialbrine, dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexanes:EtOAc 10:1 to 4:1)

Sources & evidence

ORD record: ord-281bc405bfe0464baca29d8bfcb2a785
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

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