Sodium Carbonate → HCID 22246783, compound

HRID 890728Notes

Reaction equation

HRID 890728 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.I[C:17]1[CH:39]=[CH:38][C:20]([CH2:21][N:22]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.CCO.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:39]=[CH:38][C:20]([CH2:21][N:22]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:19][CH:18]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 22246725HCID 22246725, compound

Product 1

HCID 22246783HCID 22246783, compoundYield 80.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (102 mg, 0.09 mmol), aqueous Na2CO3 (0.9 mL, 1M), and phenyl boronic acid (216 mg, 1.77 mmol) were added to a solution of ethyl 7-{[4-iodobenzyl]-methanesulfonyl-amino}-heptanoate (415 mg, 0.89 mmol) in toluene (37 mL) and EtOH (7 mL). The reaction mixture was heated at reflux for 3 h. The solution was diluted with EtOAc and was washed with water (2×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. Purification by radial chromatography (10% EtOAc/hexanes to 30% EtOAC/hexanes) provided the title compound of Step A (298 mg). 1H NMR (400 MHz, CDCl3) δ 7.62–7.30 (m, 4H), 4.41 (s, 2H), 4.12 (q, 2H), 3.20 (t, 2H), 2.82 (s, 3H), 2.23 (t, 3H), 1.58 (m, 4H), 1.35 (m, 7H); MS 418.3 (M+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. washwas washed with water (2×)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by radial chromatography (10% EtOAc/hexanes to 30% EtOAC/hexanes)

Sources & evidence

ORD record
ord-107ee68907154cc99275697a10b83b36
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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