Potassium Carbonate → HCID 58843098, compound

HRID 384862Notes

Reaction equation

HRID 384862 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12](Br)[CH:13]=2)[N:8]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:7]=1.[S:26]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].O.COCCOC>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:28]3[CH:29]=[CH:30][S:26][CH:27]=3)[CH:13]=2)[N:8]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:7]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 581760Thiophene-3-boronic acidHCID 58843093HCID 58843093, compound

Product 1

HCID 58843098HCID 58843098, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

3-(1-Benzenesulfonyl-5-bromo-1H-indol-3-yl)-propionic acid methyl ester 89 (200 mg, 0.474 mmol) was combined with 3-thienyl boronic acid (67.0 mg, 0.52 mmol), triphenylphosphine (9.0 mg, 0.03 mmol), Pd(OAc)2 (4.0 mg, 0.015 mmol), K2CO3 (90 mg, 0.65 mmol), 1,2-Dimethoxyethane (DME, 4.0 mL) and H2O (0.4 mL) and was heated at 90° C. for 48 hours. The reaction was allowed to cool to room temperature and the solvent was evaporated. The resulting residue was dissolved in EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered, and evaporated. The residue was purified with flash silica gel chromatography (20% EtOAc/Hexanes) to obtain the ester 91 as a white solid, (110 mg, M+1=426.1).

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was evaporated
  3. dissolutionThe resulting residue was dissolved in EtOAc
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified with flash silica gel chromatography (20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-cdeec98e5f064740b134e99eef322a96
Source dataset
uspto-grants-2013_02
Patent number
US08367828B2

Reaction notes

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