Acetic Acid → HCID 22632586, compound

HRID 2417535Notes

Reaction equation

HRID 2417535 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:17]([O-])=O)=[C:7]([CH:16]=1)[CH2:8][NH:9][CH2:10][C:11]([O:13]CC)=O)#[N:2].[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.C(N(CC)CC)C.[H][H].[N:39]1([C:44]([C:46]2[CH:53]=[CH:52][C:49]([CH:50]=O)=[CH:48][CH:47]=2)=[O:45])[CH2:43][CH:42]=[CH:41][CH2:40]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C.C1COCC1.[Pd]>[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:9]2[CH2:8][C:7]3[CH:16]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[N:17]([CH2:50][C:49]3[CH:48]=[CH:47][C:46]([C:44]([N:39]4[CH2:43][CH:42]=[CH:41][CH2:40]4)=[O:45])=[CH:53][CH:52]=3)[C:11](=[O:13])[CH2:10]2)=[O:26])=[CH:23][CH:22]=1

Participants

12

Reactant 7

HCID 176Acetic AcidHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589888HCID 86589888, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22632586HCID 22632586, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent4×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.1 g (16.8 mmol) of ethyl (5-cyano-2-nitrobenzyl)aminoacetate was dissolved in 100 ml of dichloromethane. 2.4 ml (19.3 mmol) of 4-chlorobenzoyl chloride and 3.6 ml (25.2 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the crude product thus obtained was dissolved in a mixture of 30 ml of ethyl acetate and 30 ml of THF. 300 mg of 10% palladium/carbon was added to the obtained solution and they were stirred in the presence of hydrogen at room temperature for 6 hours. The reaction solution was filtered through Celite. The solvent was evaporated and 1.4 g (3.8 mmol) of the obtained crude product was dissolved in 50 ml of dichloromethane. 834 mg (4.2 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde and 0.43 ml (7.6 mmol) of acetic acid were added to the obtained solution, and they were stirred at room temperature for 30 minutes. 2.0 g (9.5 mmol) of sodium triacetoxyborohydride was added to the reaction mixture, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. temperatureunder cooling with ice for 2 hours
  3. filtrationThe reaction solution was filtered through Celite
  4. customThe solvent was evaporated
  5. custom1.4 g (3.8 mmol) of the obtained crude product
  6. stirringwere stirred at room temperature for 30 minutes
  7. stirringwere stirred at room temperature overnight
  8. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-8d397b82e09f4d78948d1fbc88344c72
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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