Water → 1,1-Dimethylethyl N-((6-phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

HRID 2078214Notes

Reaction equation

HRID 2078214 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:5]2[OH:26].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[K+].[K+].O>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:27]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])=[O:16])=[C:5]3[OH:26])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67099310HCID 67099310, compound

Product 1

HCID 670999281,1-Dimethylethyl N-((6-phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinateYield 68.5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To 1,1-dimethylethyl N-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (250 mg, 658 μmol, Example 40A-D), phenylboronic acid (120 mg, 987 μmol), Pd2(dba)3 (60.3 mg, 65.8 μmol), and X-Phos (62.8 mg, 132 μmol), were added dioxane (3291 μL) and K2CO3 in water (987 μL, 1975 μmol). The reaction was then heated at 110° C. for 6 hours. The resulting reaction mixture was cooled to ambient temperature, diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 50 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (190 mg) as an amber amorphous solid after purification via prep-LC. MS (m/z)=444 (M+Na)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to ambient temperature
  3. additionadded to a separatory funnel
  4. custompartitioned with NaHCO3 (saturated, aqueous)
  5. washwashed 2 times with 50 mL of NaHCO3 (saturated, aqueous)
  6. customseparated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc626dc0a2d1433598570055988fb075
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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