Cornforth reagent → HCID 57517436, compound

HRID 84188Notes

Reaction equation

HRID 84188 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][OH:20])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH:19]=[O:20])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 57517435[1-(Phenylsulfonyl)indolin-5-yl]methanol

Product 1

HCID 57517436HCID 57517436, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

molecular sieves (0.63 g) were added to a solution of 12 (0.24 g, 0.83 mmol) in CH2Cl2 (10 mL), PDC (0.63 g, 1.66 mmol). The mixture was stirred at room temperature overnight before it was filtered through celite. The organic layer was concentrated under reduced pressure then purified by silica gel chromatography (EtOAc:n-hexane=1:2) to afford 13 (0.19 g). 1H NMR (500 MHz, CDCl3): δ 3.05 (t, J=8.6 Hz, 2H), 4.01 (t, J=8.7 Hz, 2H), 7.46-7.49 (m, 2H), 7.58-7.62 (m, 2H), 7.71 (d, J=8.3 Hz, 1H), 7.75 (d, J=8.3 Hz, 1H), 7.84 (d, J=7.8 Hz, 2H), 9.85 (s, 1H).

Workup

  1. filtrationwas filtered through celite
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthen purified by silica gel chromatography (EtOAc:n-hexane=1:2)

Sources & evidence

ORD record
ord-0a304d8884754aa69bc0064a70c4bcc3
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Reaction notes

Loading…