Potassium Carbonate → Ethyl 2-(4-chloro-1-hydroxy-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798303Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18][CH:19](C)C)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].BrC1[S:30][C:31]([N+:34]([O-:36])=[O:35])=[N:32][N:33]=1>CC#N>[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18][C:19]2[S:30][C:31]([N+:34]([O-:36])=[O:35])=[N:32][N:33]=2)[CH:3]=1

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of ethyl 2-(4-chloro-1-hydroxy-6-isopropoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (400 mg, 1.48 mmol) in MeCN (5 mL) was added anhydrous K2CO3 (414 mg, 3 mmol) and the mixture was cooled to −30° C. To this mixture was added 2-bromo-5-nitro-1,3,4-thiadiazole (420 mg, 2 mmol). The reaction mixture was stirred at −30° C. for 5 h. The reaction was quenched by addition of ice and the mixture was extracted with EtOAc (3×5 ml). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude product as a yellow oil (430 mg). MS (ESI) m/z=400 [M+H]+.

Workup

customThe reaction was quenched by addition of ice
extractionthe mixture was extracted with EtOAc (3×5 ml)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c05b88b15bb44acca62422bdbe8fa24c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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