Potassium Carbonate → 5-Bromo-3-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide

HRID 1772670Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][S:8](=[O:11])(=[O:10])[N:7]([CH3:12])[C:6]=2[CH:13]=1.C([O-])([O-])=O.[K+].[K+].[CH3:20][Si:21]([CH2:24][CH2:25][O:26][CH2:27]Cl)([CH3:23])[CH3:22]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH2:27][O:26][CH2:25][CH2:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[S:8](=[O:11])(=[O:10])[N:7]([CH3:12])[C:6]=2[CH:13]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 6-bromo-1-methyl-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide (557 mmol, 2.10 mmol, as prepared above) in DMF (5 mL), K2CO3 (1.00 g, 7.23 mmol) and SEM-Cl (0.560 mL, 3.20 mmol) were added. The resulting mixture was stirred at 75° C. for 4 h and allowed to cool to rt. The reaction mixture was diluted with water (50 mL) and extracted with DCM (3×20 mL). The combined DCM layers were dried over Na2SO4, filtered, concentrated and the resulting residue was purified by flash column chromatography on silica gel (0-50% hexane/EtOAc) to obtain compound 39a. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.12-7.17 (m, 2H), 6.60 (d, J=8.6 Hz, 1H), 5.14 (s, 2H), 3.68-3.74 (m, 2H), 3.25 (s, 3H), 0.93-0.99 (m, 3H), 0.01 (s, 9H).

Workup

temperatureto cool to rt
extractionextracted with DCM (3×20 mL)
dry with materialThe combined DCM layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customthe resulting residue was purified by flash column chromatography on silica gel (0-50% hexane/EtOAc)

Sources & evidence

ORD record: ord-4a92f0911c07434594ce8ef16473c6cc
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

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