Sodium Carbonate → HCID 68813460, compound

HRID 2104266Notes

Reaction equation

HRID 2104266 reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]([S:10][C:11]1[C:20](Br)=[CH:19][C:18]2[CH2:17][CH:16]([NH:22][C:23](=[O:25])[CH3:24])[CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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:1]([O:5][C:6](=[O:26])[C:7]([S:10][C:11]1[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:19][C:18]2[CH2:17][CH:16]([NH:22][C:23](=[O:25])[CH3:24])[CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 68813221HCID 68813221, compound

Product 1

HCID 68813460HCID 68813460, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To 2-(6-acetylamino-3-bromo-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methylpropionic acid tert-butyl ester (0.135 g; 0.30 mmol) dissolved in toluene (1.5 mL) was added phenylboronic acid (0.178 g; 1.46 mmol), Pd(PPh3)4 (15 mg; 0.013 mmol) and 2M Na2CO3 (0.61 mL) and the reaction mixture heated at 95° C. for 18 h. The reaction mixture was cooled, diluted with EtOAc, washed with H2O (2×), brine, dried over Na2SO4, filtered and the solvent removed under reduced pressure to yield a crude residue which was purified by flash chromatography (SiO2) eluting with a heptane-EtOAc gradient (50→100%) to yield 2-(6-acetylamino-3-phenyl-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl}-2-methyl-propionic acid tert-butyl ester as a clear oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with H2O (2×), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto yield a crude residue which
  7. customwas purified by flash chromatography (SiO2)
  8. washeluting with a heptane-EtOAc gradient (50→100%)

Sources & evidence

ORD record
ord-3333462a2cdf4742990f67038cb94379
Source dataset
uspto-grants-2009_08
Patent number
US07576238B2

Reaction notes

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