Cesium carbonate → 1-[2-(2-Bromoethoxy)ethyl]-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818782Notes

Reaction equation

HRID 1818782 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][S:9]1(=[O:18])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30]Br>>[Br:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[S:9]1(=[O:18])=[O:17]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 21521Bis(2-bromoethyl) etherHCID 468330941-(2-Fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

Product 1

HCID 687085361-[2-(2-Bromoethoxy)ethyl]-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideYield 67%

Procedure

In an analogous manner as described in general procedure IV, 1-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (0.22 g, 0.83 mmol) was treated with cesium carbonate (0.27 g, 0.83 mmol) and 1-Bromo-2-(2-bromo-ethoxy)-ethane (0.03 mL, 3.3 mmol) to provide 0.23 g (67%) of 1-[2-(2-bromoethoxy)ethyl]-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide. HRMS: calculated for C16H16BrFN2O3S+H+, 415.01218; found (ESI, [M+H]+), 415.0127; HPLC purity 100.0% at 210-370 nm, 10.1 minutes; Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/minutes 85/15-5/95 (Ammonium formate buffer pH=3.5/ACN+MeOH) for 10 minutes hold 4 minutes.

Sources & evidence

ORD record
ord-a0fcbc88801b4be9af30aabe396aa057
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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