4-Methylmorpholine → 3-((4-Bromo-1H-pyrazol-1-yl)methyl)benzamide

HRID 2175253Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11](O)=[O:12])[CH:6]=1.C[N:18]1CCOCC1.ClC(OCC(C)C)=O.[OH-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([NH2:18])=[O:12])[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-((4-bromo-1H-pyrazol-1-yl)methyl)benzoic acid (0.20 g, 0.711 mmol) in THF (3.5 mL) at 0° C. was added N-methylmorpholine (0.086 g, 0.854 mmol), and isobutyl chloroformate (0.107 g, 0.783 mmol) slowly. The reaction was stirred at 0° C. for 1.5 h and ammonium hydroxide (0.249 g, 7.11 mmol) was slowly added. The reaction was allowed to warm to room temperature where it stirred overnight. At the conclusion of this period, the reaction mixture was partitioned between DCM and water. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (0.188 g, 94%). LCMS, [M+H]+=280.0.

Workup

temperatureto warm to room temperature where it
stirringstirred overnight
customAt the conclusion of this period, the reaction mixture was partitioned between DCM and water
customThe organic layer was separated
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-767b103b6242468989ffc202027855be
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062028B2

Reaction notes

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