Sodium Bicarbonate → N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamide

HRID 1641570Notes

Reaction equation

HRID 1641570 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([NH:18][C:19](=[O:21])[CH3:20])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]2)=[CH:4][CH:3]=1.[CH:22]([C:24]1[S:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23].C(=O)([O-])O.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:22]([C:24]1[S:28][C:27]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]3([NH:18][C:19](=[O:21])[CH3:20])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]3)=[CH:4][CH:3]=2)=[CH:26][CH:25]=1)=[O:23]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27734305-Formyl-2-thiopheneboronic acidHCID 46202882N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide

Product 1

HCID 57624621N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamideYield 21.5%

Reagents, catalysts & solvents 3

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

Procedure

A mixed solution of N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide (1.07 g) of Reference Example 5, 5-formyl-2-thiopheneboronic acid (0.56 g), sodium hydrogen carbonate (1.51 g), palladium(II) acetate (33.7 mg) and 2-(di-t-butylphosphino)biphenyl (89.5 mg) in 1,2-dimethoxyethane (12 mL)-water (4 mL) was stirred at 65° C. for 9 hr under a nitrogen atmosphere. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.25 g) as brown crystals.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2a17d82e6e78402c8ea7b64e743f3c12
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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