Iodoethane → HCID 70980708, compound

HRID 1475335Notes

Reaction equation

HRID 1475335 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F: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].I[CH2:21][CH3:22].[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:21]([S:13]([C:10]1[CH:11]=[C:12]2[C:7]([C:6]([CH3:19])([CH3:18])[CH2:5][N:4]2[C:1](=[O:3])[CH3:2])=[CH:8][C:9]=1[F:17])(=[O:15])=[O:14])[CH3:22]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 86723952HCID 86723952, compound

Product 1

HCID 70980708HCID 70980708, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

The title compound was prepared from 1-acetyl-5-fluoro-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonyl chloride (300 mg, 0.98 mmol), iodoethane (396 μL, 4.9 mmol), Na2SO3 (236 mg, 1.87 mmol), NaHCO3 (165 mg, 1.96 mmol) and TBABr (2 mg, 0.006 mmol) following similar methods to those described in Prep 64, to give the title compound (160 mg). 1H NMR (CDCl3): 8.67 (1H, d), 6.98 (1H, d), 3.86 (2H, s), 3.38-3.19 (2H, m), 2.22 (3H, s), 1.38 (6H, s), 1.34-1.27 (3H, m).

Sources & evidence

ORD record
ord-2d65645741544bf9bef242622ea22f4e
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

Loading…