Potassium Hydroxide → HCID 58081154, compound

HRID 1841968Notes

Reaction equation

HRID 1841968 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C1(C)C=CC(S(O[CH:21]2[CH2:30][CH2:29][C:24]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:23][CH2:22]2)(=O)=O)=CC=1.[OH-].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:21]1[CH2:30][CH2:29][C:24]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:23][CH2:22]1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 249055-BromoindoleHCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)

Product 1

HCID 58081154HCID 58081154, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-bromoindole (8.472 g, 43.216 mmol), [CAS: 10075-50-0]), toluene-4-sulfonic acid, 1,4-dioxa-spiro[4.5]dec-8-yl ester (13.5 g, 43.216 mmol) [C.A.S. 23551-05-9]; (prepared according to the procedure described in J. Chem. Soc., Perkin Trans. 1 2002, 20, 2251-2255) and powdered potassium hydroxide (13.239 g, 235.958 mmol) in DMSO (300 ml) was stirred at 80° C. for 6 h. Subsequently, the mixture was cooled to room temperature and poured into ice water. The resulting aqueous mixture was extracted with Et2O, dried (Na2SO4), and the volatiles were evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; DCM/heptane 1:1 as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D11 (2.897 g, 19.93%) as a white solid.

Workup

  1. custom(prepared
  2. extractionThe resulting aqueous mixture was extracted with Et2O
  3. dry with materialdried (Na2SO4)
  4. customthe volatiles were evaporated in vacuo
  5. customThe crude residue was purified by column chromatography (silica gel; DCM/heptane 1:1 as eluent)
  6. customThe desired fractions were collected
  7. concentrationconcentrated in vacuo
  8. customto yield intermediate compound D11 (2.897 g, 19.93%) as a white solid

Sources & evidence

ORD record
ord-6719b08203104dbb9fa597c0959f9f42
Source dataset
uspto-grants-2015_02
Patent number
US08946205B2

Reaction notes

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