Cesium carbonate → [4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]boronic acid

HRID 2423536Notes

Reaction equation

Cl[CH2:2][C:3]1[C:4]([C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[N:5][O:6][C:7]=1[CH:8]([CH3:10])[CH3:9].C(=O)([O-])[O-].[Cs+].[Cs+].[SH:25][C:26]1[CH:31]=[CH:30][C:29]([B:32]([OH:34])[OH:33])=[CH:28][CH:27]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[C:4]1[C:3]([CH2:2][S:25][C:26]2[CH:31]=[CH:30][C:29]([B:32]([OH:34])[OH:33])=[CH:28][CH:27]=2)=[C:7]([CH:8]([CH3:10])[CH3:9])[O:6][N:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole (152 mg, 0.5 mmol), cesium carbonate (489 mg, 1.5 mmol) and 4-mercaptophenyl boronic acid (75 mg, 0.5 mmol) in dimethylformamide (5 mL) was allowed to stir for 24 hours in a 60° C. oil bath. The mixture was diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried with magnesium sulfate, filtered and concentrated to yield 277 mg of crude [4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]boronic acid and dimethylformamide. 1H NMR (400 MHz, d6-DMSO): δ 7.63-7.59 (m, 4H), 7.55-7.51 (m, 1H), 7.17 (d, J=8 Hz, 2H), 3.86 (s, 2H), 3.12 (septet, J=7 Hz, 1H), 1.13 (d, J=7 Hz, 6H).

Workup

washwashed with water
washThe organic layer was washed with brine
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-640dbdae7d2846bcb1aaa1bae87b82f7
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960552B2

Reaction notes

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