Potassium Carbonate → HCID 24813854, compound

HRID 1183790Notes

Reaction equation

HRID 1183790 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]=[O:32])=[CH:27][CH:26]=2)[C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[C:18]([OH:24])[CH:17]=2)=[CH:11][CH:10]=1)=[O:8].Br[CH:34]([CH2:40][CH3:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C=O)C>[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:25]2[CH:26]=[CH:27][C:28]([CH:31]=[O:32])=[CH:29][CH:30]=2)[C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[C:18]([CH:17]=2)[O:24][CH2:41][CH2:40][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:11][CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 24814389Benzaldehyde, 4-[bis(4-formylphenyl)amino]-2-hydroxy-

Product 1

HCID 24813854HCID 24813854, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (1.1 g, 8.0 mmol, 10 eq.) is added to a solution of compound 10 (280 mg, 810 μmol) in dry DMF (12 mL). The reaction is stirred for 15 minutes and ethyl bromobutanoate (175 μL, 1.22 mmol, 1.5 eq.) is slowly added. The mixture is stirred for 24 hours at room temperature and then concentrated. The residue is taken up in dichloromethane and water. The two-phase mixture is allowed to separate by settling, and the organic phase is washed several times with water. After drying and concentrating, a solid is obtained which is purified by chromatography (elution with a methanol gradient from 0 to 1% in dichloromethane) to give 275 mg (530 μmol) of compound 11 in the form of an orange powder (yield: 75%).

Workup

  1. stirringThe mixture is stirred for 24 hours at room temperature
  2. concentrationconcentrated
  3. customto separate
  4. washthe organic phase is washed several times with water
  5. customAfter drying
  6. concentrationconcentrating
  7. customa solid is obtained which
  8. customis purified by chromatography (
  9. washelution with a methanol gradient from 0 to 1% in dichloromethane)

Sources & evidence

ORD record
ord-7273ab6f1c1043388855c27647937ed2
Source dataset
uspto-grants-2014_03
Patent number
US08664400B2

Reaction notes

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