Potassium Carbonate → 1-Boc-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-methoxyindole

HRID 506083Notes

Reaction equation

HRID 506083 reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[C:9]1B(O)O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].I[C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:33][CH2:32][CH2:31][S:30]2(=[O:35])=[O:34])=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[C:9]1[C:23]1[CH:24]=[CH:25][C:26]([N:29]2[CH2:33][CH2:32][CH2:31][S:30]2(=[O:35])=[O:34])=[CH:27][CH:28]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 147632212-(4-Iodophenyl)isothiazolidine-1,1-dioxideHCID 223094576-Methoxy-1H-indole-2-boronic acid, N-BOC protected

Product 1

HCID 594306781-Boc-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-methoxyindoleYield 98%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-Boc-6-methoxyindole-2-boronic acid prepared in step B above (0.36 g, 1.25 mmol), 2-(4-iodophenyl)isothiazolidine-1,1-dioxide (0.32 g, 1.0 mmol) and PdCl2(dppf) (0.037 g, 0.05 mmol) in DMF (4.0 mL), is added aqueous K2CO3 solution (1.5 mL, 2.0 M, 3.0 mmol). The mixture is stirred at room temperature overnight and then poured into ice-water (100 mL). The precipitate is collected and washed with water and purified by flash column chromatography (silica gel, DCM/EtOAc, 9/1) to furnish 1-Boc-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-methoxy-1H-indole (0.43 g, 98%).

Workup

  1. customThe precipitate is collected
  2. washwashed with water
  3. custompurified by flash column chromatography (silica gel, DCM/EtOAc, 9/1)

Sources & evidence

ORD record
ord-f54a24dca0344fe78a34346f3e8ec831
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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