Sodium Hydroxide → 4-benzyloxy-1-(2-fluorobenzenesulfonyl)-1H-indole

To a magnetically stirred mixture of 4-benzyloxyindole (13.80 g, 0.062 mol), tetrabutylammonium hydrogen sulfate (1.05 g, 0.0031 mol) and finely ground sodium hydroxide (2.72 g, 0.068 mol) in 100 mL of dichloromethane at 0° C., was added 2-fluorobenzenesulfonyl chloride (13.25 g, 0.068 mol). After 18 hours stirring at ambient temperature, 2-fluorobenzenesulfonyl chloride (3.96 g, 0.020 mol) and finely ground sodium hydroxide (0.82 g, 0.020) were added. One hour later, the reaction mixture was washed sequentially with water (2×100 ML) and an aqueous K2CO3 solution (2 M, 100 mL). The aqueous fractions were combined and extracted with CH2Cl2 (2×45 mL). The organic fractions were combined, dried over MgSO4 and concentrated in vacuo. The resulting solid was recrystallized from 10:2 ethyl acetate/hexanes (100 mL) to give 4-benzyloxy-1-(2-fluorobenzenesulfonyl)-1H-indole as an off-white powder (21.48 g, 91%). MP 117-120° C.

1. washOne hour later, the reaction mixture was washed sequentially with water (2×100 ML)
2. extractionextracted with CH2Cl2 (2×45 mL)
3. dry with materialdried over MgSO4
4. concentrationconcentrated in vacuo
5. customThe resulting solid was recrystallized from 10:2 ethyl acetate/hexanes (100 mL)

ORD-Eintrag

ord-f1877373559348c79650b8eb14559a6f

Quelldatensatz

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06774241B2