Sodium Bicarbonate → HCID 59009237, compound

HRID 545111Notes

Reaction equation

HRID 545111 reaction equation
Br[C:2]1[S:3][C:4]([S:7][CH2:8][C:9]([NH:11][CH2:12][C@@H:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:14]2)=[O:10])=[CH:5][CH:6]=1.[N:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>COCCOC.O>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[Cl:26])[CH2:19][N:15]1[CH2:16][CH2:17][O:18][C@@H:13]([CH2:12][NH:11][C:9](=[O:10])[CH2:8][S:7][C:4]2[S:3][C:2]([C:31]3[CH:32]=[CH:33][N:28]=[CH:29][CH:30]=3)=[CH:6][CH:5]=2)[CH2:14]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 59009243HCID 59009243, compound

Product 1

HCID 59009237HCID 59009237, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

The resultant product (500 mg) of Example 31 and 4-pyridylboronic acid (250 mg) were dissolved in a mixed solvent of ethylene glycol dimethyl ether (25 mL) and water (5 mL), sodium hydrogen carbonate (500 mg) and tetrakistriphenylphosphine palladium (60 mg) were added, and the mixture was stirred overnight at 100° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent, and the obtained residue was recrystallized from ethyl acetate to give the title compound (90 mg) as a pale-brown powder.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography
  7. customThe solvent was evaporated from the eluent
  8. customthe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eb21b9fed0394a30b1b6152c679ae58a
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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