HCID 67240989, compound → HCID 67241531, compound

HRID 2423178Notes

Reaction equation

HRID 2423178 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:20]CC4C=CC=CC=4)=[C:16]([F:19])[CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[F:19][C:16]1[CH:17]=[C:18]2[C:13]([CH:12]=[CH:11][N:10]2[S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:14][C:15]=1[OH:20]

Participants

4

Reactant 1

HCID 67240989HCID 67240989, compound2×

Product 1

HCID 67241531HCID 67241531, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd/C 10 wt. % (250 mg, 0.236 mmol was added to a solution of N-benzenesulfonyl-5-benzyloxy-6-fluoroindole (Intermediate 27, 250 mg, 6.55 mmol) in ethanol (100 mL). The reaction mixture was stirred under an atmosphere of hydrogen (1 atm) at room temperature for 2 hours, filtered and evaporated. The crude material was purified by flash chromatography on silica gel using 0.5% MeOH/DCM as the eluent to give the title compound (1.79 g) as a white solid. MS m/z 292 [M+H]+.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe crude material was purified by flash chromatography on silica gel using 0.5% MeOH/DCM as the eluent

Sources & evidence

ORD record
ord-9e51b765d94941018f158365a2042934
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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