Ethanol → HCID 59314334, compound

HRID 1047844Notes

Reaction equation

HRID 1047844 reaction equation
C([NH:4][C:5]1[C:10]([C:11]([NH:13][C:14]2([C:23]([OH:25])=[O:24])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:12])=[C:9]([CH:26]=[C:27]([CH3:29])[CH3:28])[C:8]([CH3:30])=[CH:7][CH:6]=1)(=O)C.C([O-])([O-])=O.[K+].[K+].[CH3:37][CH2:38]O>[Pd]>[CH2:37]([O:25][C:23]([C:14]1([NH:13][C:11](=[O:12])[C:10]2[C:5]([NH2:4])=[CH:6][CH:7]=[C:8]([CH3:30])[C:9]=2[CH:26]=[C:27]([CH3:28])[CH3:29])[CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22]1)=[O:24])[CH3:38]

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 59314256HCID 59314256, compound

Product 1

HCID 59314334HCID 59314334, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

To a solution of (223) (278 mg, 0.67 mmol) and 2,2-dimethylethyleneboronic acid (134 mg, 1.34 mmol) in 10 ml EtOH is added palladium anchored homogeneous catalyst, FibreCatPd(0), (4.84% Pd, 195 mg, 0.089 mmol) and 2M aqueous solution of K2SO4 (1.78 mL, 3.56 mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 110° C., 5 h. After concentration in vacuo, the residue is purified by HPLC to give 380 mg brown semi-solid (224).

Workup

  1. customThe resulting reaction mixture
  2. customrun in a microwave reaction
  3. custom110° C., 5 h
  4. concentrationAfter concentration in vacuo
  5. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-3998424b23b84c7daf8422c60ec30b2b
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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