Potassium Carbonate → HCID 57678938, compound

HRID 491856Notes

Reaction equation

HRID 491856 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[C:5]2[OH:22].C(=O)([O-])[O-].[K+].[K+].[CH3:29][O:30][C:31](=[O:34])[CH2:32]Br>C(#N)C>[CH3:29][O:30][C:31](=[O:34])[CH2:32][O:22][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[N:7]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 57678934HCID 57678934, compound

Product 1

HCID 57678938HCID 57678938, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 5-bromo-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-ol (21, 130 mg, 0.340 mmol) in acetonitrile (3.5 mL) in a high pressure reaction vessel was added potassium carbonate (235 mg, 1.70 mmol) and bromoacetic acid methyl ester (38.6 μL, 0.408 mmol). The vessel was flushed with a nitrogen atmosphere, sealed with a Teflon stopcock and heated to 80° C. for overnight. After the reaction mixture was cooled to 25° C., ethyl acetate was added and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated at reduced pressure to obtain a light brown solid. Purification of the crude material was carried out using biotage chromatography (30% ethyl acetate in hexanes) which afforded the product as an off-white solid (22, 72.0 mg, 47% yield). MS(ESI) [M+H+]+=454.2; 456.2.

Workup

  1. customThe vessel was flushed with a nitrogen atmosphere
  2. customsealed with a Teflon stopcock
  3. temperatureAfter the reaction mixture was cooled to 25° C.
  4. additionethyl acetate was added
  5. washwashed with saturated sodium bicarbonate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated at reduced pressure
  9. customto obtain a light brown solid
  10. customPurification of the crude material

Sources & evidence

ORD record
ord-bf1f30ac43444d24be1c0cc30741934e
Source dataset
uspto-grants-2009_05
Patent number
US07531568B2

Reaction notes

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