HCID 66786963, compound → HCID 59577683, compound

HRID 1947460Notes

Reaction equation

HRID 1947460 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([CH2:20][OH:21])[NH:17]2)=[CH:13][CH:12]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([CH:20]=[O:21])[NH:17]2)=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 66786963HCID 66786963, compound

Product 1

HCID 59577683HCID 59577683, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [6-(benzothiazol-2-yloxy)-1H-indol-2-yl]-methanol (97 mg, 0.32 mmol) in CHCl3 (5 mL) was added MnO2 (280 mg, 3.2 mmol) and heated (80° C., 2 h). The reaction mixture was cooled (rt), filtered (Celite®) and washed with EtOAc (100 mL). The organic layer was washed with brine (50 mL), dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using EtOAc:hexane (0-50%) to provide the title compound as beige solid (47 mg, 49%). MS (ESI): mass calcd. for C16H10N2O2S, 294.1; m/z found, 295.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 9.80 (s, 1H), 9.80 (s, 1H), 7.79 (d, J=8.8, 1H), 7.73 (d, J=8.1, 1H), 7.68 (d, J=8.0, 1H), 7.49 (s, 1H), 7.40 (dd, J=11.3, 4.1, 1H), 7.31-7.24 (m, 2H), 7.15 (dd, J=8.8, 2.1, 1H).

Workup

  1. temperatureThe reaction mixture was cooled (rt)
  2. filtrationfiltered (Celite®)
  3. washwashed with EtOAc (100 mL)
  4. washThe organic layer was washed with brine (50 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-a0368b88ed81449fbb3e525ca0de8436
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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