3-Amino-5-methylisoxazole → 1-(5-Methylisoxazol-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 1626577Notes

Reaction equation

[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.ClC(Cl)(O[C:21](=[O:27])OC(Cl)(Cl)Cl)Cl.[CH3:29][C:30]1[O:34][N:33]=[C:32]([NH2:35])[CH:31]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1.C(Cl)Cl.C(Cl)Cl>[CH3:29][C:30]1[O:34][N:33]=[C:32]([NH:35][C:21]([NH:13][C:12]2[CH:14]=[CH:15][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)=[O:27])[CH:31]=1

Participants

Conditions

Temperature: 20 °C

Procedure

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (100 mg, 0.46 mmol), and triphosgene (47 mg, 0.16 mmol) were dissolved in a mixture of dry pyridine:DCM (4:1) and stirred at room temperature (20° C.) under nitrogen atmosphere for 1 h. 5-methylisoxazol-3-amine (49 mg, 0.50 mmol) dissolved in dry DCM was added dropwise, and stirring allowed overnight. Saturated NaHCO3 solution was added to the reaction mixture, and stirring allowed for 15 mins before partitioning between water and DCM. The organic layer was recovered, dried over MgSO4, filtered and solvent removed in vacuo, affording the title compound (155 mg, 0.45 mmol, 99% yield).

Workup

additionwas added dropwise
stirringstirring
waitallowed overnight
stirringstirring
waitallowed for 15 mins
custombefore partitioning between water and DCM
customThe organic layer was recovered
dry with materialdried over MgSO4
filtrationfiltered
customsolvent removed in vacuo

Sources & evidence

ORD record: ord-6b8b888b773a4dc5b1617d3da984e290
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785457B2

Reaction notes

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