Sodium Carbonate → HCID 18507797, compound

HRID 1355668Notes

Reaction equation

HRID 1355668 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:32][C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)([CH2:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[C:7](=[O:24])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH:45]([C:47]1[CH:52]=[CH:51][C:50](B(O)O)=[CH:49][CH:48]=1)=[O:46]>C1(C)C=CC=CC=1.CCO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:45]([C:47]1[CH:52]=[CH:51][C:50]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([CH2:25][C:26]4[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=4)([CH2:32][C:33]4[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=4)[C:7](=[O:24])[N:8]3[CH2:11][C:12]3[CH:17]=[CH:16][C:15]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:14][CH:13]=3)=[CH:4][CH:3]=2)=[CH:49][CH:48]=1)=[O:46]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 18507756HCID 18507756, compound

Product 1

HCID 18507797HCID 18507797, compoundYield 80.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-(6-Bromo-2-oxo-3,3-bis-pyridin-4-ylmethyl-2,3-dihydro-indol-1-ylmethyl)-N,N-dimethyl-benzenesulfonamide (306 mg, 0.517 mmol) was dissolved in a solution of 6 ml of toluene and 1 ml of EtOH under an atmosphere of dry N2. To this solution was added tetrakis(triphenylphosphine)palladium (0) (34 mg, 0.029 mmol) followed by a solution of Na2CO3 (126 mg, 1.19 mmol) dissolved in 1 ml of water and 4-formylbezeneboronic acid (116 mg, 0.776 mmol). The reaction mixture was heated to 100° C. and reacted at this temperature overnight. The reaction mixture was cooled to ambient temperature and then partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was washed two more times with EtOAc. The combined EtOAc layers were dried over Na2SO4, filtered and concentrated under vacuum to give a dark oil. The oil was purified using radial chromatography eluting with MeOH/DCM (5:95) to give 258 mg of the titled compound as a solid.

Workup

  1. customreacted at this temperature overnight
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. custompartitioned between EtOAc and saturated aqueous NaHCO3
  4. washThe aqueous layer was washed two more times with EtOAc
  5. dry with materialThe combined EtOAc layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto give a dark oil
  9. customThe oil was purified
  10. washeluting with MeOH/DCM (5:95)

Sources & evidence

ORD record
ord-7100ec5c7db94175a82af1b28a7546f3
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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