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

HRID 1835914Notes

Reaction equation

HRID 1835914 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27](Cl)(=[O:29])=[O:28]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[F:20])(=[O:29])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 884654-(phenylmethoxy)-1H-indoleHCID 1377612-Fluorobenzenesulphonyl chloride2×

Product 1

HCID 121489984-benzyloxy-1-(2-fluorobenzenesulfonyl)-1H-indoleYield 91%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f1877373559348c79650b8eb14559a6f
Source dataset
uspto-grants-2004_08
Patent number
US06774241B2

Reaction notes

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