Iodoethane → 1-(5-Bromo-6-ethanesulfonyl-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone

HRID 1475320Notes

Reaction equation

[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:17])=[C:10]([S:13](Cl)(=[O:15])=[O:14])[CH:11]=2)[C:6]([CH3:19])([CH3:18])[CH2:5]1)(=[O:3])[CH3:2].[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+].I[CH2:32][CH3:33]>O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[Br:17][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[S:13]([CH2:32][CH3:33])(=[O:15])=[O:14])[N:4]([C:1](=[O:3])[CH3:2])[CH2:5][C:6]2([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 105 °C

Procedure

A suspension of 1-acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonyl chloride (300 mg, 0.81 mmol), Na2SO3 (206 mg, 1.6 mmol) and NaHCO3 (134 mg, 1.6 mmol) in water (5 mL) was stirred at 105° C. for 1.5 h. The resulting solution was cooled to 70° C., then TBABr (1.5 mg, 0.005 mmol) and iodoethane (323 μL, 4 mmol) were added and the stirring maintained at the same temperature for 4 h. The reaction mixture was cooled to ambient temperature, diluted with water (15 mL) and extracted with DCM (3×). The organic phase was dried (MgSO4), filtered and concentrated and the crude material was purified using SiO2 chromatography (50% EtOAc/Petrol) to give the title compound (0.21 g) as a pale yellow oil. 1H NMR (CDCl3): 8.92 (1H, s), 7.45 (1H, s), 3.87 (2H, s), 3.43 (2H, q), 2.23 (3H, s), 1.39 (6H, s), 1.33-1.26 (3H, m).

Workup

temperatureThe resulting solution was cooled to 70° C.
temperaturethe stirring maintained at the same temperature for 4 h
temperatureThe reaction mixture was cooled to ambient temperature
extractionextracted with DCM (3×)
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customthe crude material was purified

Sources & evidence

ORD record: ord-8d48fbdfef9f4108a569f234f5d7a8ce
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018214B2

Reaction notes

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